Trifluoroacetic acid methylene chloride → 2-amino-N-[4-methyl-6-(2-phenylethynyl)pyridin-2-yl]propanamide

HRID 535431Notes

Reaction equation

HRID 535431 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([C:19]#[C:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694421tert-butyl-N-[1-[[4-methyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Product 1

HCID 866944222-amino-N-[4-methyl-6-(2-phenylethynyl)pyridin-2-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-[1-[[4-methyl-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate D3b (2 mg, 5 μmol) and DCM:TFA (9:1, 400 μl) is stirred at RT for 4 hours. 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. Yield: 1.5 mg (quant.). HPLC-MS: M+H=280; tR=1.77 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

Sources & evidence

ORD record
ord-3dbe1318ad5941dab524fb1d3f8ee009
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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