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

HRID 1397403Notes

Reaction equation

HRID 1397403 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.[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:26]([C:29]2[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[O:31][N:30]=2)=[CH:25][C:21]=1[C:22](O)=[O:23]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:15][C:22](=[O:23])[C:21]3[CH:25]=[C:26]([C:29]4[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[O:31][N:30]=4)[CH:27]=[CH:28][C:20]=3[O:19][CH3:18])[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 673230862-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amineHCID 673256512-Methoxy-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 71244920N-(2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropyl)-2-methoxy-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamideYield 36%

Procedure

This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine and 2-methoxy-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6 (40 mg, yield 36%). 1H NMR (400 MHz, MeOD) δ 8.64-8.63 (d, J=2.3 Hz, 1H), 8.45-8.42 (t, J=5.6 Hz, 1H), 8.24-8.21 (dd, J=8.8 Hz, 2.4 Hz, 1H), 8.11-8.07 (m, 2H), 7.83 (s, 1H), 7.34-7.32 (d, J=8.8 Hz, 1H), 7.27-7.23 (t, J=8.8 Hz, 2H), 3.91 (s, 3H), 3.72-3.71 (m, 2H), 1.41 (s, 6H). MS (ESI) m/z: Calculated for C24H20F4N4O4: 504.14. found: 505.2 (M+H)+.

Sources & evidence

ORD record
ord-ffa37534c5c84424b0f276f95ee0ab69
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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