3-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid → HCID 53345242, compound

HRID 1397422Notes

Reaction equation

HRID 1397422 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[O:9][CH:10]=1)[OH:5].[F:18][C:19]([F:35])([F:34])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])[N:21]=1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[O:9][CH:10]=[C:6]([CH:4]([OH:5])[CH2:3][CH2:2][NH:1][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([C:22]4[N:21]=[C:20]([C:19]([F:35])([F:34])[F:18])[O:24][N:23]=4)[CH:26]=3)[N:7]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67323046HCID 67323046, compound

Product 1

HCID 53345242HCID 53345242, compoundYield 19%

Procedure

This compound was synthesized from 3-amino-1-(2-(4-fluorophenyl)oxazol-4-yl)propan-1-ol and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (35 mg, yield 19%) as a white solid. 1H NMR (400 MHz, DMSO-d6) 8.80-8.77 (t, J=5.3 Hz, 1H), 8.51 (s, 1H), 8.20-8.18 (d, J=7.6 Hz, 1H), 8.13-8.11 (d, J=7.9 Hz, 1H), 8.00 (s, 1H), 7.99-7.96 (dd, J=8.8 Hz, 5.5 Hz, 2H), 7.72-7.68 (t, J=7.8 Hz, 1H), 7.37-7.32 (t, J=8.8 Hz, 2H), 5.44-5.43 (d, J=5.2 Hz, 1H), 4.69-4.65 (m, 1H), 3.47-3.42 (m, 2H), 2.17-2.08 (m, 1H), 1.99-1.90 (m, 1H). MS (ESI) m/z: Calculated for C22H16F4N4O4: 476.11. found: 477.1 (M+H)+.

Sources & evidence

ORD record
ord-7c7172bcd1914d9ab3256a0e2cc105bf
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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