p-Toluenesulfonic acid → 3-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2,3-dihydroxy-propyl ester

HRID 18685Notes

Reaction equation

HRID 18685 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:33]#[N:34])=[C:18]([NH:20][C:21](=[O:32])[CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])[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.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:33]#[N:34])=[C:18]([NH:20][C:21](=[O:32])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[S:19][C:13]=2[CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 118574333-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine 6-carboxylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Product 1

HCID 118574353-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2,3-dihydroxy-propyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 131723227HCID 131723227, compoundSolvent

Procedure

0,26 mmol of 3-Cyano-2-[3-(2-methoxy-phenyl)-propanoylamino]-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (Example 30) 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-8bac8248aca14084b58c87e4277a6cee
Source dataset
uspto-grants-2010_06
Patent number
US07741488B2

Reaction notes

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