2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine → 2-Fluoro-N-(2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide

HRID 1397385Notes

Reaction equation

HRID 1397385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=1.[F:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]2[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[O:30][N:29]=2)=[CH:24][C:20]=1[C:21](O)=[O:22]>>[F:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]2[N:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[O:30][N:29]=2)=[CH:24][C:20]=1[C:21]([NH:15][CH2:14][C:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:9][CH:10]=1)([CH3:17])[CH3:16])=[O:22]

Participants

3

Reactant 2

HCID 673230862-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amineHCID 673238992-Fluoro-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 699503732-Fluoro-N-(2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropyl)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 32%

Procedure

This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine and 2-fluoro-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (75 mg, yield 32%) as a yellow viscous liquid. 1H NMR (400 MHz, MeOD) δ 8.46-8.43 (dd, J=6.8 Hz, 2.3 Hz, 1H), 8.29-8.25 (ddd, J=8.7 Hz, 4.8 Hz, 2.4 Hz, 1H), 8.09-8.05 (dd, J=9.0 Hz, 5.3 Hz, 2H), 7.77 (s, 1H), 7.47-7.42 (dd, J=10.3 Hz, 8.8 Hz, 1H), 7.25-7.20 (t, J=8.9 Hz, 2H), 3.67 (s, 2H), 1.41 (s, 6H). MS (ESI) m/z: Calculated for C23H17F6N4O3: 492.12. found: 493.2 (M+H)+.

Sources & evidence

ORD record
ord-a616e4058cd641669c81194338747ac1
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…