Methanol → tert-butyl-N-[1-[(1-ethynylisoquinolin-3-yl)amino]-1-oxopropan-2-yl]-carbamate

HRID 535396Notes

Reaction equation

HRID 535396 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([CH3:28])[C:9](=[O:27])[NH:10][C:11]1[N:12]=[C:13]([C:21]#[C:22][Si](C)(C)C)[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].CO>O>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([CH3:28])[C:9]([NH:10][C:11]1[N:12]=[C:13]([C:21]#[CH:22])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:27])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 86694376tert-butyl-N-[1-oxo-1-[[1-(2-trimethylsilylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate

Product 1

HCID 86694379tert-butyl-N-[1-[(1-ethynylisoquinolin-3-yl)amino]-1-oxopropan-2-yl]-carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl-N-[1-oxo-1-[[1-(2-trimethylsilylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate C4a (319 mg, 0.78 mmol), aqueous 1 N KOH solution (3 ml) and MeOH (10 ml) is stirred at RT for 2 h. The mixture is diluted with water and extracted with EtOAc. The combined organic layers are dried over Na2SO4 and concentrated in vacuo and the product purified by RP HPLC. Yield: 225 mg (86%). HPLC-MS: M+H=340; tR=1.84 min (*Method—1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-c2212c0fe56b4a61857c0b77b86b9983
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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