Palupiprant

C₂₂H₁₈F₅N₃O₄CAS 1369489-71-3483.40 g/mol

Open in Covalent MOL file

Alkyl halide Amide Carboxylic acid Ether

Properties

Molecular formula: C₂₂H₁₈F₅N₃O₄
Molar mass: 483.40 g/mol
Exact mass: 483.1217 Da
logP: 5.36Crippen estimate
Polar surface area: 93.5 Å²
H-bond donors / acceptors: 2 / 4
Rotatable bonds: 7
Stereocentres: Sin SMILES atom order

Hazards

No GHS classification is on file for this compound. That is not evidence that it is harmless.

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Identifiers

CAS number

1369489-71-3

SMILES

C[C@@H](C1=CC=C(C=C1)C(=O)O)NC(=O)C2=C(N(N=C2C(F)F)C)OC3=CC=CC(=C3)C(F)(F)F

InChIKey

MKLKAQMPKHNQPR-NSHDSACASA-N

InChI

InChI=1S/C22H18F5N3O4/c1-11(12-6-8-13(9-7-12)21(32)33)28-19(31)16-17(18(23)24)29-30(2)20(16)34-15-5-3-4-14(10-15)22(25,26)27/h3-11,18H,1-2H3,(H,28,31)(H,32,33)/t11-/m0/s1

Characterization data

Calculated from the structure, in the form journals print them.

¹H NMR

Predicted ¹H NMR (400 MHz, CDCl₃) δ 11.50 (br s, 1H), 8.60 (t, J(H,F) = 47.0 Hz, 1H), 8.21 (d, J = 7.7 Hz, 2H), 7.54 (d, J = 7.7 Hz, 2H), 7.45 (m, J = 7.7 Hz, 1H), 7.45 (m, J = 7.7, 1.6 Hz, 1H), 7.39 (t, J = 1.6 Hz, 1H), 7.27 (dt, J = 7.7, 1.6 Hz, 1H), 5.90 (br d, J = 5.0 Hz, 1H), 5.12 (qd, J = 7.0, 5.0 Hz, 1H), 3.65 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H).

¹³C NMR

Predicted ¹³C NMR (101 MHz, CDCl₃) δ 172.7, 166.8, 157.9, 157.6, 148.4, 140.4 (t, J(C,F) = 32.5 Hz), 131.3 (q, J(C,F) = 32.5 Hz), 130.0, 129.1, 128.7, 126.9, 124.3 (q, J(C,F) = 272.0 Hz), 122.3, 120.0 (q, J(C,F) = 3.8 Hz), 115.8 (q, J(C,F) = 3.8 Hz), 115.5 (t, J(C,F) = 240.0 Hz), 97.5 (t, J(C,F) = 3.8 Hz), 53.9, 33.2, 26.3.

[M + H]+

[M + H]+ Calcd for C22H19F5N3O4 484.1290

[M + Na]+

[M + Na]+ Calcd for C22H18F5N3NaO4 506.1110

[M − H]−

[M − H]− Calcd for C22H17F5N3O4 482.1145

Elemental analysis

Anal. Calcd for C22H18F5N3O4: C, 54.66; H, 3.75; N, 8.69.