Triethylamine → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(3-methoxy-azetidin-1-yl)-pyridin-3-yl]-amide

HRID 2236316Notes

Reaction equation

HRID 2236316 reaction equation
[CH3:1][O:2][CH:3]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=2)[CH2:4]1.[C:16]1([C:22]2[O:23][C:24]([C:30]([F:33])([F:32])[F:31])=[C:25]([C:27](O)=[O:28])[N:26]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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][O:2][CH:3]1[CH2:6][N:5]([C:7]2[N:8]=[CH:9][C:10]([NH:13][C:27]([C:25]3[N:26]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:23][C:24]=3[C:30]([F:32])([F:33])[F:31])=[O:28])=[CH:11][CH:12]=2)[CH2:4]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 593013622-(3-Methoxy-azetidin-1-yl)-5-nitro-pyridine

Product 1

HCID 593014062-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(3-methoxy-azetidin-1-yl)-pyridin-3-yl]-amideYield 21.5%

Procedure

2-(3-Methoxy-azetidin-1-yl)-5-nitro-pyridine (120 mg, 0.5 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (141 mg, 0.55 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-(3-methoxy-azetidin-1-yl)-pyridin-3-yl]-amide as a light green solid (45 mg). ES-MS calcd for C20H17F3N4O3 (m/e) 418.38, obsd 419.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f263081b4c614b4ebbcfd1ca4ddbc7bb
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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