HCID 22616369, compound → HCID 22616370, compound

HRID 1870528Notes

Reaction equation

HRID 1870528 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH3:38])[CH:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[CH:26][CH:25]=4)=[O:22])=[CH:16][C:15]=3[CH:39]=2)=[CH:7][CH:6]=1)=[O:4]>CO.C1COCC1.[OH-].[Na+]>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([C:21]([NH:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH3:38])[CH:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[CH:26][CH:25]=4)=[O:22])=[CH:16][C:15]=3[CH:39]=2)=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

5

Reactant 1

HCID 22616369HCID 22616369, compound

Product 1

HCID 22616370HCID 22616370, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-(4-methoxycarbonylphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.25 g) in methanol (25 ml), THF (25 ml) and 1N NaOH (5 ml) was refluxed overnight. The reaction mixture was concentrated, and neutralized using 1N HCl. The precipitate was filtered, washed with water and dried to give 2-(4-carboxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.21 g) as colorless amorphous.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-98d91063279442708f0f78bd2a168fac
Source dataset
uspto-grants-2000_08
Patent number
US06096780

Reaction notes

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