2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine → 5-(5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropyl)nicotinamide

HRID 1397398Notes

Reaction equation

HRID 1397398 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][CH:19]([F:34])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[N:27][CH:28]=[C:29]([CH:33]=2)[C:30](O)=[O:31])[N:21]=1>>[F:34][CH:19]([F:18])[C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[N:27][CH:28]=[C:29]([CH:33]=2)[C:30]([NH:15][CH2:14][C:13]([C:11]2[N:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:9][CH:10]=2)([CH3:17])[CH3:16])=[O:31])[N:21]=1

Participants

3

Reactant 2

HCID 673230862-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amineHCID 673239365-(5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

Product 1

HCID 699499925-(5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl)-N-(2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropyl)nicotinamideYield 24%

Procedure

This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine and 5-(5-(difluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid as described in example 8 step 6 (45 mg, yield 24%). 1H NMR (400 MHz, DMSO-d6) δ 9.32 (d, J=2.1 Hz, 1H), 9.20 (d, J=2.1 Hz, 1H), 8.82-8.78 (m, 1H), 8.75-8.74 (t, J=2.1 Hz, 1H), 8.04-8.00 (m, 3H), 7.74-7.48 (m, 1H), 7.38-7.33 (t, J=8.9 Hz, 2H), 3.55-3.53 (d, J=6.1 Hz, 2H), 1.31 (s, 6H). MS (ESI) m/z: Calculated for C22H18F3N5O3: 457.14. found: 458.2 (M+H)+.

Sources & evidence

ORD record
ord-77762697fcde4e5eb0b920ab47585519
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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