Triethylamine → 2-Phenyl-5-trifluoromethyloxazole-4-carboxylic Acid[6-(3-Ethoxyazetidin-1-yl)pyridin-3-yl]amide

HRID 2236318Notes

Reaction equation

HRID 2236318 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=2)[CH2:5]1)[CH3:2].[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>>[CH2:1]([O:3][CH:4]1[CH2:7][N:6]([C:8]2[N:9]=[CH:10][C:11]([NH:14][C:28]([C:26]3[N:27]=[C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:24][C:25]=3[C:31]([F:33])([F:34])[F:32])=[O:29])=[CH:12][CH:13]=2)[CH2:5]1)[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 593012812-(3-Ethoxy-azetidin-1-yl)-5-nitro-pyridine

Product 1

HCID 529367272-Phenyl-5-trifluoromethyloxazole-4-carboxylic Acid[6-(3-Ethoxyazetidin-1-yl)pyridin-3-yl]amideYield 69.2%

Procedure

2-(3-Ethoxy-azetidin-1-yl)-5-nitro-pyridine (59 mg, 0.264 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (74 mg, 0.29 mmol), Et3N (186 uL, 1.32 mmol) and BOP (122 mg. 0.277 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-ethoxy-azetidin-1-yl)-pyridin-3-yl]-amide as a solid (79 mg). ES-MS calcd for C21H19F3N4O3 (m/e) 432.41, obsd 433.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-24a3125592b14b96a7cfcd0ae5eb8b9b
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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