Trifluoroacetic acid methylene chloride → 3-[6-(2-Aminopropanoylamino)-2-(2-phenylethynyl)pyridin-3-yl]-benzoic acid

HRID 535417Notes

Reaction equation

HRID 535417 reaction equation
CC(OC([NH:8][CH:9]([CH3:36])[C:10]([NH:12][C:13]1[N:18]=[C:17]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([OH:32])=[O:31])=[CH:15][CH:14]=1)=[O:11])=O)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[NH2:8][CH:9]([CH3:36])[C:10]([NH:12][C:13]1[N:18]=[C:17]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]2[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=2)[C:30]([OH:32])=[O:31])=[CH:15][CH:14]=1)=[O:11]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 866944043-[6-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]benzoic acid

Product 1

HCID 866944063-[6-(2-Aminopropanoylamino)-2-(2-phenylethynyl)pyridin-3-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-[6-[2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]benzoic acid E2c (16 mg, 0.03 mmol) and DCM:TFA (9:1, 1.7 ml) is stirred at RT for 90 minutes. The mixture is diluted with toluene (10 ml) and concentrated in vacuo. The product is purified by RP HPLC. Yield: 3 mg (24%). HPLC-MS: M+H=386; tR=1.03 min (*Method—1).

Workup

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

Sources & evidence

ORD record
ord-7e5c3cf3f4e3431998057f6a74c1dec0
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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