Triethylamine → HCID 59301446, compound

HRID 2236319Notes

Reaction equation

HRID 2236319 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH2:7][N:8]([CH3:18])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)[CH2:3][CH2:2]1.[C:19]1([C:25]2[O:26][C:27]([C:33]([F:36])([F:35])[F:34])=[C:28]([C:30](O)=[O:31])[N:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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]1([CH2:4][O:5][CH2:6][CH2:7][N:8]([CH3:18])[C:9]2[N:10]=[CH:11][C:12]([NH:15][C:30]([C:28]3[N:29]=[C:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[O:26][C:27]=3[C:33]([F:35])([F:36])[F:34])=[O:31])=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301375HCID 59301375, compound

Product 1

HCID 59301446HCID 59301446, compoundYield 63.3%

Procedure

(2-Cyclopropylmethoxy-ethyl)-methyl-(5-nitro-pyridin-2-yl)-amine (82 mg, 0.326 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (92 mg, 0.359 mmol), Et3N (229 uL, 1.63 mmol) and BOP (151 mg. 0.326 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-[(2-cyclopropylmethoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide as a solid (95 mg). ES-MS calcd for C23H23F3N4O3 (m/e) 460.46, obsd 461.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-27c1b725806b474f8e8ae245e99765b5
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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