2-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amine → N-(2-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropyl)-5-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)nicotinamide

HRID 1397401Notes

Reaction equation

HRID 1397401 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:37])([F:36])[C:20]([C:22]1[S:26][C:25]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:35]=2)[C:32](O)=[O:33])=[CH:24][CH:23]=1)=[O:21]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:15][C:32](=[O:33])[C:31]3[CH:35]=[C:27]([C:25]4[S:26][C:22]([C:20](=[O:21])[C:19]([F:36])([F:18])[F:37])=[CH:23][CH:24]=4)[CH:28]=[N:29][CH:30]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 673237882-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amineHCID 673255045-(5-(2,2,2-Trifluoroacetyl)thiophen-2-yl)nicotinic acid

Product 1

HCID 67324048N-(2-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropyl)-5-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)nicotinamideYield 20%

Procedure

This compound was synthesized from 2-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)-2-methylpropan-1-amine and 5-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)nicotinic acid as described in example 8 step 6 (28 mg, yield 20%) as a yellow viscous liquid. 1H NMR (400 MHz, DMSO-d6) δ 9.20 (d, J=2.3 Hz, 1H), 9.01-8.98 (m, 1H), 8.80-8.77 (m, 1H), 8.51-8.48 (m, 1H), 8.21-8.19 (m, 1H), 8.01-7.96 (m, 4H), 7.24-7.19 (m, 2H), 3.59-3.57 (d, J=6.2 Hz, 2H), 1.42 (s, 6H). MS (ESI) m/z: Calculated for C24H19F4N6O2S: 517.12. found: 516.4 (M−H)−.

Sources & evidence

ORD record
ord-f8bb2567dd074689a0924fb6d1f02ecb
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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