p-Toluenesulfonic acid → HCID 59306436, compound

HRID 1717451Notes

Reaction equation

HRID 1717451 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]3[C:17]([C:31]#[N:32])=[C:18]([NH:20][C:21](=[O:30])/[CH:22]=[CH:23]/[C:24]4[CH:29]=C[CH:27]=[CH:26][CH:25]=4)[S:19][C:13]=3[CH2:12]2)=[O:10])[CH2:4][O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.C([N:47](CC)CC)C>C(C#N)(C)=O.O>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[C:17]([C:31]#[N:32])=[C:18]([NH:20][C:21](=[O:30])/[CH:22]=[CH:23]/[C:24]3[CH:29]=[N:47][CH:27]=[CH:26][CH:25]=3)[S:19][C:13]=2[CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 59306305HCID 59306305, compound

Product 1

HCID 59306436HCID 59306436, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 131723227HCID 131723227, compoundSolvent

Procedure

0.26 mmol of 3-Cyano-2-((E)-3-phenyl-allanoylamino)-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester are dissolved in 10 ml AcCN/H2O (2/1) and 0.1 eq PTSA is added. After stirring over night, some triethylamine is added and the solvent removed. Recrystallization from ethanol gives the desired product in 80% yield.

Workup

  1. customthe solvent removed
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-c44d76c706c34d4cb27ce70db78dec89
Source dataset
uspto-grants-2010_09
Patent number
US07803945B2

Reaction notes

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