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

HRID 535428Notes

Reaction equation

HRID 535428 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[C:16]([Cl: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]([Cl: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]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694418tert-butylN-[1-[[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate

Product 1

HCID 866944192-amino-N-[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butylN-[1-[[4-chloro-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate D3a (20 mg, 0.05 mmol) and DCM:TFA (9:1, 1.8 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: 14 mg (93%). HPLC-MS: M+H=300; tR=1.92 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-92499e1f2df949aa8e367d85c3b622cc
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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