Diisopropylethylamine → 1-(2-Oxo-2-thiophen-2-yl-acetyl)piperidine-2-carboxylic acid N'-(6-methyl-4-trifluoromethyl-pyridin-2-yl)-hydrazide

HRID 7905Notes

Reaction equation

HRID 7905 reaction equation
[O:1]=[C:2]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]([OH:18])=O)[C:3](=[O:9])[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.[NH:19]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([CH3:31])[N:22]=1)[NH2:20].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:31][C:23]1[N:22]=[C:21]([NH:19][NH:20][C:16]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[C:2](=[O:1])[C:3](=[O:9])[C:4]2[S:5][CH:6]=[CH:7][CH:8]=2)=[O:18])[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 27756841-(6-Methyl-4-(trifluoromethyl)-2-pyridyl)hydrazineHCID 98168041-[1,2-Dioxo-2-(thien-2-yl)ethyl)-2-piperidinecarboxylic acid

Product 1

HCID 101381351-(2-Oxo-2-thiophen-2-yl-acetyl)piperidine-2-carboxylic acid N'-(6-methyl-4-trifluoromethyl-pyridin-2-yl)-hydrazide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

From Intermediate 3 (267 mg, 1 mmol), 2-hydrazino-6-methyl-4-trifluoromethylpyridine (191 mg, 1 mmol), PyBrop (466 mg, 1 mmol), DMAP (122 mg) and DIEA (2 mL) in THF (30 mL), using the same procedure for Compound 1, the title compound was obtained as a white solid; 110 mg (25%). MS (m/z) 441 (M+1).

Sources & evidence

ORD record
ord-617a12e0035e4410b97f42be63d9aec7
Source dataset
uspto-grants-2006_08
Patent number
US07087628B2

Reaction notes

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