Pyridine → 7-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-5-ethyl-6,7-dihydro-5H-thieno[3,2-b]pyridine-4-carboxylic acid isopropyl ester

HRID 2378100Notes

Reaction equation

HRID 2378100 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH:8]([O:11][C:12]([N:14]1[CH:19]([CH2:20][CH3:21])[CH2:18][CH:17]([NH:22][CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[C:16]2[S:38][CH:39]=[CH:40][C:15]1=2)=[O:13])([CH3:10])[CH3:9].N1C=CC=CC=1>ClCCl>[CH:8]([O:11][C:12]([N:14]1[CH:19]([CH2:20][CH3:21])[CH2:18][CH:17]([N:22]([C:1](=[O:3])[CH3:2])[CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:27]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:25]=2)[C:16]2[S:38][CH:39]=[CH:40][C:15]1=2)=[O:13])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 589267187-(3,5-bis-trifluoromethyl-benzylamino)-5-ethyl-6,7-dihydro-5H-thieno[3,2-b]pyridine-4-carboxylic acid isopropyl ester

Product 1

HCID 115701097-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-5-ethyl-6,7-dihydro-5H-thieno[3,2-b]pyridine-4-carboxylic acid isopropyl esterYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Inject acetic anhydride (0.250 ml, 2.65 mmol) dropwise to a solution of crude 7-(3,5-bis-trifluoromethyl-benzylamino)-5-ethyl-6,7-dihydro-5H-thieno[3,2-b]pyridine-4-carboxylic acid isopropyl ester (0.120 g, 0.243 mmol) and pyridine (0.250 ml, 3.10 mmol) in dichloromethane (1 ml) at room temperature. Stir the mixture at room temperature for 16 h. Evaporate the solvents and purify the resulting reside using silica gel column chromatography (gradient eluent, 0-35% ethyl acetate in hexane) to provide the title compound (0.0290 g, 22%). MS (ES+): 559 (M+Na); (ES−): 535 (M−H). cl Example 2

Workup

  1. customat room temperature
  2. customEvaporate the solvents
  3. custompurify the resulting reside

Sources & evidence

ORD record
ord-40d15568d37d44878dd25200596002ba
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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