Trifluoroacetic acid methylene chloride → 2-amino-N-[1-[2-(1,3-thiazol-4-yl)ethynyl]isoquinolin-3-yl]propan-amide

HRID 535436Notes

Reaction equation

HRID 535436 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[N:24]=[CH:25][S:26][CH:27]=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>C(Cl)Cl>[NH2:7][CH:8]([CH3:29])[C:9]([NH:10][C:11]1[N:12]=[C:13]([C:21]#[C:22][C:23]2[N:24]=[CH:25][S:26][CH:27]=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 86694426tert-butyl-N-[1-oxo-1-[[1-[2-(1,3-thiazol-4-yl)ethynyl]isoquinolin-3-yl]-amino]propan-2-yl]carbamate

Product 1

HCID 717149272-amino-N-[1-[2-(1,3-thiazol-4-yl)ethynyl]isoquinolin-3-yl]propan-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[1-oxo-1-[[1-[2-(1,3-thiazol-4-yl)ethynyl]isoquinolin-3-yl]-amino]propan-2-yl]carbamate E4b (12 mg, 0.03 mmol) and DCM:TFA (9:1, 3 ml) is stirred at RT for 1 h. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 2 mg (22%). HPLC-MS: M+H=323; tR=1.65 min (*Method—1).

Workup

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-5812ea608e414948ae8e212be2773c2b
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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