Triethylamine → HCID 72251197, compound

HRID 2236317Notes

Reaction equation

HRID 2236317 reaction equation
[CH:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)([CH2:3][CH3:4])[CH3:2].[C:15]1([C:21]2[O:22][C:23]([C:29]([F:32])([F:31])[F:30])=[C:24]([C:26](O)=[O:27])[N:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>>[CH:1]([NH:5][C:6]1[N:7]=[CH:8][C:9]([NH:12][C:26]([C:24]2[N:25]=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:22][C:23]=2[C:29]([F:31])([F:32])[F:30])=[O:27])=[CH:10][CH:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 43078820HCID 43078820, compound

Product 1

HCID 72251197HCID 72251197, compoundYield 41%

Procedure

sec-Butyl-(5-nitro-pyridin-2-yl)-amine (97.5 mg, 0.5 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (135 mg, 0.525 mmol), Et3N (352 uL, 2.5 mmol) and BOP (232 mg. 0.525 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-sec-butylamino-pyridin-3-yl)-amide as a light purple solid (83 mg). ES-MS calcd for C20H19F3N4O2 (m/e) 404.40, obsd 405.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-445713033de34e3d8ecbfca4306efca8
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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