Triethylamine → HCID 59301396, compound

HRID 2236315Notes

Reaction equation

HRID 2236315 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]([CH3:16])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=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][CH2:4][CH2:5][N:6]([CH3:16])[C:7]1[N:8]=[CH:9][C:10]([NH:13][C:28]([C:26]2[N:27]=[C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:24][C:25]=2[C:31]([F:33])([F:34])[F:32])=[O:29])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301393HCID 59301393, compound

Product 1

HCID 59301396HCID 59301396, compoundYield 67.1%

Procedure

(2-Ethoxy-ethyl)-methyl-(5-nitro-pyridin-2-yl)-amine (150 mg, 0.666 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (171 mg, 0.666 mmol), Et3N (464 uL, 3.3 mmol) and BOP (309 mg. 0.699 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-ethoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide as a yellow solid (194 mg). ES-MS calcd for C21H21F3N4O3 (m/e) 434.42, obsd 435.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-0c0c6d63e0f944b9bf0f9dee5003d4c8
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

Loading…