Triethylamine → HCID 59301399, compound

HRID 2236323Notes

Reaction equation

HRID 2236323 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:21])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]1([C:29]2[O:30][C:31]([C:37]([F:40])([F:39])[F:38])=[C:32]([C:34](O)=[O:35])[N:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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>>[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][CH2:9][CH2:10][N:11]([CH3:21])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:34]([C:32]2[N:33]=[C:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:30][C:31]=2[C:37]([F:39])([F:40])[F:38])=[O:35])=[CH:14][N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 59301401HCID 59301401, compound

Product 1

HCID 59301399HCID 59301399, compoundYield 30.2%

Procedure

{2-[Methyl-(5-nitro-pyridin-2-yl)-amino]-ethoxy}-acetic acid tert-butyl ester (218 mg, 0.7 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (189 mg, 0.735 mmol), Et3N (394 uL, 2.8 mmol) and BOP (325 mg. 0.735 mmol). Following work-up as above, the crude material was purified by flash chromatography to yield [2-(methyl-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-amino)-ethoxy]-acetic acid tert-butyl ester as a solid (110 mg). ES-MS calcd for C25H27F3N4O5 (m/e) 520.51, obsd 521.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-5780e0c3f8014701b3b584cf84c9b84e
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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