Triethylamine → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(bicyclo[2.2.1]hept-2-ylamino)-pyridin-3-yl]-amide

HRID 2236326Notes

Reaction equation

HRID 2236326 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=1.[C:18]1([C:24]2[O:25][C:26]([C:32]([F:35])([F:34])[F:33])=[C:27]([C:29](O)=[O:30])[N:28]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[N:10]=[CH:11][C:12]([NH:15][C:29]([C:27]2[N:28]=[C:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:25][C:26]=2[C:32]([F:34])([F:35])[F:33])=[O:30])=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301448HCID 59301448, compound

Product 1

HCID 593013702-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(bicyclo[2.2.1]hept-2-ylamino)-pyridin-3-yl]-amideYield 17%

Procedure

Bicyclo[2.2.1]hept-2-yl-(5-nitro-pyridin-2-yl)-amine (102 mg, 0.4 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (123 mg, 0.48 mmol), Et3N (281 uL, 2 mmol) and BOP (194 mg. 0.444 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-(bicyclo[2.2.1]hept-2-ylamino)-pyridin-3-yl]-amide as a light purple solid (30 mg). ES-MS calcd for C23H21F3N4O2 (m/e) 442.44, obsd 443.2 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-44327e11d8cb43e5a7de4ce007a293c6
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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