Water → N-(2-chlorophenyl)-N-methyl-8-((methylamino)methyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84537Notes

Reaction equation

HRID 84537 reaction equation
[CH3:1][NH2:2].Br[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[C:14]3[S:15][C:16]([C:18]([N:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])[CH3:21])=[O:19])=[CH:17][C:13]=3[CH2:12][CH2:11][O:10][C:9]=2[CH:29]=1.O>CCO>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:20]([CH3:21])[C:18]([C:16]1[S:15][C:14]2[C:8]3[CH:7]=[CH:6][C:5]([CH2:4][NH:2][CH3:1])=[CH:29][C:9]=3[O:10][CH2:11][CH2:12][C:13]=2[CH:17]=1)=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 568341528-(Bromomethyl)-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Product 1

HCID 56833639N-(2-chlorophenyl)-N-methyl-8-((methylamino)methyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamideYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of CH3NH2 in EtOH (0.25 mL) was added TEA (0.5 mL) and 8-(bromomethyl)-N-(2-chlorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (250 mg). The reaction mixture was stirred for 2 h at 60° C. before added water. The mixture was extracted with EtOAc (20 mL×3), dried over Na2SO4 and filtered. The filtrate was concentrated to give the crude product, which was purified by preparative TLC (CH2Cl2: MeOH=10:1) to afford 243 as a light yellow solid (95.6 mg, 42.8%). MS: (ESI+) 412.9

Workup

  1. extractionThe mixture was extracted with EtOAc (20 mL×3)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC (CH2Cl2: MeOH=10:1)

Sources & evidence

ORD record
ord-c27482514a644eb29b062a43a70e9937
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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