Trifluoroacetic acid methylene chloride → N-[5-benzyl-6-(2-phenylethynyl)pyridin-2-yl]-2-(methylamino)-propan-amide

HRID 535419Notes

Reaction equation

HRID 535419 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([CH3:34])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:15]([C:26]#[C:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]=1)=[O:11])C)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[CH:9]([NH:7][CH3:6])[CH3:34])=[N:14][C:15]=1[C:26]#[C:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694407tert-butyl-N-[1-[[5-benzyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]-N-methylcarbamate

Product 1

HCID 86694408N-[5-benzyl-6-(2-phenylethynyl)pyridin-2-yl]-2-(methylamino)-propan-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-benzyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate E2d (26 mg, 0.6 mmol) and DCM:TFA (9:1, 2 ml) is stirred at RT for 90 minutes. 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: 4 mg (20%). HPLC-MS: M+H=370; tR=2.16 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-ea864f6818a94960b828430fdd131b87
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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