Water → tert-butyl 4-((2-((benzyloxy)carbonyl)hydrazino)carbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1-carboxylate

HRID 1897957Notes

Reaction equation

HRID 1897957 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[N:29]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:28]=[CH:27][CH:26]=3)[N:19]=2)([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:34]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)(=[O:37])[NH:35][NH2:36].Cl.CN(C)CCCN=C=NCC.O>C(Cl)(Cl)Cl>[CH2:39]([O:38][C:34]([NH:35][NH:36][C:14]([C:11]1([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[N:29]([C:30]([CH3:33])([CH3:31])[CH3:32])[N:28]=[CH:27][CH:26]=3)[N:19]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1)=[O:16])=[O:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79242Benzyl carbazateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668909961-(tert-butoxycarbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-4-carboxylic acid

Product 1

HCID 66889476tert-butyl 4-((2-((benzyloxy)carbonyl)hydrazino)carbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 535 mg of 1-(tert-butoxycarbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-4-carboxylic acid in 10 ml of chloroform were added 214 mg of benzyl carbazate and 291 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at room temperature, followed by stirring the reaction mixture at room temperature for 2 hours. The reaction mixture was poured into water, and extracted with chloroform. The chloroform solution was dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=10/1) to give the title compound as a pale brown solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-4450a269cedb4e7fa350b55a085a0a53
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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