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

HRID 535426Notes

Reaction equation

HRID 535426 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:20]([CH3:26])=[N:21][CH:22]=[N:23][C:24]=2[CH3:25])=[C:15]([C:27]#[C:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[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>[CH3:25][C:24]1[C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[CH:9]([NH:7][CH3:6])[CH3:39])=[N:14][C:15]=2[C:27]#[C:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)=[C:20]([CH3:26])[N:21]=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694415HCID 86694415, compound

Product 1

HCID 86694417N-[5-(4,6-dimethylpyrimidin-5-yl)-6-(2-naphthalen-2-ylethynyl)-pyridin-2-yl]-2-(methylamino)propanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-(4,6-dimethylpyrimidin-5-yl)-6-(2-naphthalen-2-yl-ethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate E2g (12 mg, 0.02 mmol) and DCM:TFA (9:1, 5 ml) is stirred at RT for 60 minutes. The mixture is diluted with toluene (10 ml) and concentrated in vacuo. The product is purified by RP HPLC. Yield: 6 mg (61%). HPLC-MS: M+H=436; tR=1.38 min (*Method—1).

Workup

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

Sources & evidence

ORD record
ord-b51e82b3ab704264aae4ea670cd49771
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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