Pyridine → HCID 11541196, compound

HRID 2378106Notes

Reaction equation

HRID 2378106 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[N:22]=2)[CH:17]([NH:25][CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=2)[CH2:16][CH:15]1[CH2:41][CH3:42])=[O:13])([CH3:10])[CH3:9].N1C=CC=CC=1>ClCCl>[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[N:22]=2)[CH:17]([N:25]([C:1](=[O:3])[CH3:2])[CH2:26][C:27]2[CH:28]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=2)[CH2:16][CH:15]1[CH2:41][CH3:42])=[O:13])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58926731HCID 58926731, compound

Product 1

HCID 11541196HCID 11541196, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Inject acetic anhydride (0.250 ml, 2.65 mmol) dropwise to a solution of crude 4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-7-methyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid isopropyl ester (0.090 g, 0.199 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 using silica gel column chromatography (gradient eluent, 0-40% ethyl acetate in hexane) to provide the title compound (0.0650 g, 66%). MS (ES+): 546 (M+H).

Workup

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

Sources & evidence

ORD record
ord-17de0b687ba34fb2952e6d1f8cbce7fa
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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