Trifluoroacetic acid methylene chloride → 2-amino-N-[1-(2-thiophen-3-ylethynyl)isoquinolin-3-yl]propanamide

HRID 535434Notes

Reaction equation

HRID 535434 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:29])[C:9](=[O:28])[NH:10][C:11]1[N:12]=[C:13]([C:21]#[C:22][C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[NH2:7][CH:8]([CH3:29])[C:9]([NH:10][C:11]1[N:12]=[C:13]([C:21]#[C:22][C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:28]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694425tert-butyl-N-[1-oxo-1-[[1-(2-thiophen-3-ylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate

Product 1

HCID 717149192-amino-N-[1-(2-thiophen-3-ylethynyl)isoquinolin-3-yl]propanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl-N-[1-oxo-1-[[1-(2-thiophen-3-ylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate E4a (102 mg, 0.24 mmol) and DCM:TFA (9:1, 2 ml) is stirred at RT for 1 h. The mixture is diluted with toluene (10 ml) and concentrated in vacuo. The product is purified by RP HPLC. Yield: 65 mg (84%). HPLC-MS: M+H=322; tR=1.84 min (*Method—1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-bccd8345fcd44d21b9fce4c11c068f6c
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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