Triethylamine → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid {6-[methyl-(3-methyl-butyl)-amino]-pyridin-3-yl}-amide

HRID 2236324Notes

Reaction equation

HRID 2236324 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][N:4]=1.[C:17]1([C:23]2[O:24][C:25]([C:31]([F:34])([F:33])[F:32])=[C:26]([C:28](O)=[O:29])[N:27]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>>[CH3:1][N:2]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]1[N:4]=[CH:5][C:6]([NH:9][C:28]([C:26]2[N:27]=[C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:24][C:25]=2[C:31]([F:33])([F:34])[F:32])=[O:29])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301378Methyl-(3-methyl-butyl)-(5-nitro-pyridin-2-yl)-amine

Product 1

HCID 593014562-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid {6-[methyl-(3-methyl-butyl)-amino]-pyridin-3-yl}-amideYield 7.6%

Procedure

Methyl-(3-methyl-butyl)-(5-nitro-pyridin-2-yl)-amine (110 mg, 0.49 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (138 mg, 0.54 mmol), Et3N (352 uL, 2.5 mmol) and BOP (227 mg. 0.514 mmol). Following work-up as above, the crude material was purified by flash chromatography to yield 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid {6-[methyl-(3-methyl-butyl)-amino]-pyridin-3-yl}-amide as a light purple solid (16 mg). ES-MS calcd for C22H23F3N4O2 (m/e) 432.51, obsd 433.2 M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-82724fafe460419caff8bb7da4c7c700
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

Loading…