p-Toluenesulfonic acid → HCID 11682790, compound

HRID 2236087Notes

Reaction equation

HRID 2236087 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:29]#[N:30])=[C:18]([NH:20][C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:22])[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(CC)CC)C>C(C#N)(C)=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:29]#[N:30])=[C:18]([NH:20][C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:22])[S:19][C:13]=2[CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 11719155HCID 11719155, compound

Product 1

HCID 11682790HCID 11682790, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

0.26 mmol of 3-Cyano-2-[(1-phenyl-methanoyl)-amino]-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/H20 (2/1) and 0.1 eq PTSA is added. After stirring over night, some triethylamine is added and the solvent removed. Recrystalization from ethanol gives the desired product in 80% yield.

Workup

  1. additionis added
  2. customthe solvent removed
  3. customRecrystalization from ethanol

Sources & evidence

ORD record
ord-352d7a9e33584e098a83259a32b69739
Source dataset
uspto-grants-2010_05
Patent number
US07714134B2

Reaction notes

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