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

HRID 535421Notes

Reaction equation

HRID 535421 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:31])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:14]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:13]=1)=[O:10])(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([CH3:31])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[C:14]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694409tert-butyl-N-[1-[[5-cyclopentyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Product 1

HCID 866944102-amino-N-[5-cyclopentyl-6-(2-phenylethynyl)pyridin-2-yl]-propan-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[5-cyclopentyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate E2e (18 mg, 0.04 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: 13 mg (94%). HPLC-MS: M+H=334; tR=2.09 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-d75d0cb236334cecbf1901f4594e1645
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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