Isobutyl chloroformate → N-((S)-1-((S)-1-amino-4-methyl-1-oxopentan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide

HRID 242476

Reaction equation

HRID 242476 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[C@H:3]([NH:7][C:8]([N:10]1[C:18]2[CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][C:13]=2[C:12]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:11]1)=[O:9])[C:4]([OH:6])=O.CCN(C(C)C)C(C)C.C(OC(Cl)=O)C(C)C.[NH2:48][C@H:49]([C:54]([NH2:56])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52]>C(Cl)Cl>[NH2:56][C:54](=[O:55])[C@@H:49]([NH:48][C:4](=[O:6])[C@@H:3]([NH:7][C:8]([N:10]1[C:18]2[CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][C:13]=2[C:12]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:11]1)=[O:9])[C:2]([CH3:30])([CH3:1])[CH3:29])[CH2:50][CH:51]([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 62365Isobutyl chloroformateHCID 69640LeucinamideHCID 81531Diisopropylethylamine2×HCID 46861922(S)-3,3-dimethyl-2-(5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamido)butanoic acid

Product 1

HCID 46861923N-((S)-1-((S)-1-amino-4-methyl-1-oxopentan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 71 (40 mg) in DCM was added DIEA (45 uL) followed by isobutylchloroformate (26 uL). After stirring at room temperature for 30 min, leucine amide (18 mg) and DIEA (25 uL) was added and stirred for 1 h. The reaction mixture was evaporated and dissolved in MeOH, and purified with a preparative LC-MS to give compound 72. LCMS (+ESI) m/z=537.3 [M+H]+.

Workup

  1. stirringstirred for 1 h
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in MeOH
  4. custompurified with a preparative LC-MS

Sources & evidence

ORD record
ord-eda2cff38ef04079b11b8b7e41454a5d
Source dataset
uspto-grants-2014_02
Patent number
US08653127B2

Linked notes

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