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Pyridine → N2-(2-chloro-4-(dimethylcarbamoyl)phenyl)-N8-ethyl-N2-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

HRID 1949900
Notes
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Reaction equation

HRID 1949900 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[N:13]([CH3:33])[C:14]([C:16]1[S:32][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][C:21]=3[O:22][CH2:23][CH2:24][C:18]=2[CH:17]=1)=[O:15].[CH2:34]([NH2:36])[CH3:35].N1C=CC=CC=1>O=S(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[O:12])[N:9]([CH3:10])[CH3:11])[CH:5]=[CH:4][C:3]=1[N:13]([CH3:33])[C:14]([C:16]1[S:32][C:19]2[C:20]3[CH:28]=[CH:27][C:26]([C:29]([NH:36][CH2:34][CH3:35])=[O:30])=[CH:25][C:21]=3[O:22][CH2:23][CH2:24][C:18]=2[CH:17]=1)=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 6341EthylamineHCID 568342692-((2-Chloro-4-(dimethylcarbamoyl)phenyl)(methyl) carbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carboxylic acid

Product 1

HCID 57900236N2-(2-chloro-4-(dimethylcarbamoyl)phenyl)-N8-ethyl-N2-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamideYield 31%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
95 °C

Procedure

2-((2-Chloro-4-(dimethylcarbamoyl)phenyl)(methyl)carbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carboxylic acid (0.15 g, 0.31 mmol) was dissolved in SOCl2 (10 mL). The solution was heated at 90-100° C. for 3 hours. Removal of the rest SOCl2 gave the crude product. A solution of the crude acid chloride in THF (12 mL) was treated with a solution of ethanamine (0.14 g, 3.1 mmol) and Pyridine (0.3 mL) in THF (8 mL) at 0° C. The reaction mixture was allowed to reach room temperature and stirred overnight. Concentrated to remove THF to afford the crude product, it was purified by preparative TLC to obtain 347 (48.5 mg, 31%). ESI-MS: 512. 1H NMR (CDCl3, 400 MHz): δ7.59 (s, 1H, ArH), 7.44-7.32 (m, 5H, ArH), 6.95 (s, 1H, ═CH), 6.12 (s, 1H, NH), 4.23 (t, J=5.0 Hz, 2H, CH2), 3.51-3.44 (m, 2H, CH2), 3.39 (s, 3H, CH3), 3.13 (s, 3H, CH3), 3.05 (t, J=5.0 Hz, 2H, CH2), 3.02 (s, 3H, CH3), 1.24 (t, J=7.2 Hz, 3H, CH3).

Workup

  1. customRemoval of the rest SOCl2
  2. customgave the crude product
  3. customto reach room temperature
  4. concentrationConcentrated
  5. customto remove THF
  6. customto afford the crude product, it
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-43f353c8ebd447379621f818ce9b53f5
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399690B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes