Triethylamine → HCID 59301423, compound

HRID 2236325Notes

Reaction equation

HRID 2236325 reaction equation
[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=1)[CH2:3][CH2:4][C:5]#[N:6].[C:16]1([C:22]2[O:23][C:24]([C:30]([F:33])([F:32])[F:31])=[C:25]([C:27](O)=[O:28])[N:26]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:5]([CH2:4][CH2:3][N:2]([CH3:1])[C:7]1[N:8]=[CH:9][C:10]([NH:13][C:27]([C:25]2[N:26]=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:23][C:24]=2[C:30]([F:32])([F:33])[F:31])=[O:28])=[CH:11][CH:12]=1)#[N:6]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 28387482HCID 28387482, compound

Product 1

HCID 59301423HCID 59301423, compoundYield 34.7%

Procedure

3-[Methyl-(5-nitro-pyridin-2-yl)-amino]-propionitrile (103 mg, 0.5 mmol) was hydrogenated as above and reacted with 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (108 mg, 0.423 mmol), Et3N (297 uL, 2.11 mmol) and BOP (196 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-[(2-cyano-ethyl)-methyl-amino]-pyridin-3-yl}-amide as a solid (61 mg). ES-MS calcd for C20H16F3N5O2 (m/e) 415.38, obsd 416.1 (M+H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-97774f1b3d2a4e6b92434335e5fa8802
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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