Trifluoroacetic acid methylene chloride → N-[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)pyridin-2-yl]-2-(methylamino)propanamide

HRID 535409Notes

Reaction equation

HRID 535409 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([CH3:39])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[CH:21][C:20]=2[CH3:26])=[C:15]([C:27]#[C:28][C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][CH:33]=[CH:32]3)[N:14]=1)=[O:11])C)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[CH3:26][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH3:25])[C:19]=1[C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[CH:9]([NH:7][CH3:6])[CH3:39])=[N:14][C:15]=1[C:27]#[C:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][CH:33]=[CH:32]2

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694394tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

Product 1

HCID 86694396N-[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)pyridin-2-yl]-2-(methylamino)propanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-(2-quinolin-6-ylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate G1a (28 mg, 0.05 mmol) and DCM:TFA (8:2, 10 ml) is stirred at RT for 15 minutes. The mixture is diluted with toluene (10 ml) and concentrated in vacuo. The product is purified by RP HPLC. Yield: 16 mg (70%). HPLC-MS: M+H=436; tR=1.09 min (*Method—1).

Workup

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

Sources & evidence

ORD record
ord-de37c1895870420f802aca7833fc821a
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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