2-Pyrazinecarboxylic acid → Methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoate

HRID 424968Notes

Reaction equation

HRID 424968 reaction equation
[CH:1]1([CH:7]([NH2:23])[CH:8]([NH:13][CH:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]([O:17][CH3:18])=[O:16])[C:9]([F:12])([F:11])[F:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:24]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[C:30](O)=[O:31].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl.C(OCC)(=O)C>[CH:1]1([CH:7]([NH:23][C:30]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][N:24]=2)=[O:31])[CH:8]([NH:13][CH:14]([C:19]([CH3:20])([CH3:22])[CH3:21])[C:15]([O:17][CH3:18])=[O:16])[C:9]([F:12])([F:11])[F:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66704763Methyl 2-(3-amino-3-cyclohexyl-1,1,1-trifluoropropan-2-ylamino)-3,3-dimethylbutanoate

Product 1

HCID 66705176Methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the 6A1-isomer A of methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-aminopropan-2-ylamino)-3,3-dimethylbutanoate (389 mgm), pyrazinecarboxylic acid (65 mg), 1-ethyl-3-(3′-dimethylaminopropyl)-carbodimide ((331 mg), 1-hydroxy-benzotriazole (233 mg), and N-methylmorpholine (0.19 mL) in dichloromethane was stirred at room temperature for 24 hours. The reaction mixture was then diluted with ethyl acetate and washed successively with 1N hydrochloric acid, water, brine and then dried over anhydrous sodium sulfate. Evaporation to dryness under reduced pressure gave crude methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-(pyrazine-2-carboxamido)propan-2-ylamino)-3,3-dimethylbutanoate, an isomer of a compound of formula (7) designated as 7A1-isomer A.

Workup

  1. washwashed successively with 1N hydrochloric acid, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customEvaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-3bde83de8e5d4a82b8481d081af6a4e5
Source dataset
uspto-grants-2012_01
Patent number
US08106059B2

Reaction notes

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