Tert-butyl 1-(aminomethyl)cyclobutane-1-carboxylate → 1-{[(1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl ester

HRID 1481188Notes

Reaction equation

HRID 1481188 reaction equation
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[C:25]([O:29][C:30]([C:32]1([CH2:36][NH2:37])[CH2:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CCO>[C:25]([O:29][C:30]([C:32]1([CH2:36][NH:37][C:3]([C:5]2[N:6]=[C:7]([C:23]#[N:24])[C:8]3[C:13]([C:14]=2[OH:15])=[CH:12][CH:11]=[C:10]([S:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=3)=[O:4])[CH2:33][CH2:34][CH2:35]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 66797588Tert-butyl 1-(aminomethyl)cyclobutane-1-carboxylateHCID 898128781-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester

Product 1

HCID 898130461-{[(1-Cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-methyl}-cyclobutanecarboxylic acid tert-butyl esterYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester (43 mg) and 1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester (48 mg) in EtOH (0.5 mL) was microwaved at 140° C. for 1 h. The mixture was cooled, concentrated and the residue was column purified to give the desired product (58 mg). LC MS ESI+: 490 (M+1)+.

Workup

  1. customwas microwaved at 140° C. for 1 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-9eebe6de82bd4f8c8152a228a507b508
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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