Hydrochloric Acid → N2-(2-chloro-5-(piperazine-1-carbonyl)phenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

HRID 1849255Notes

Reaction equation

HRID 1849255 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[N:24]([CH3:45])[C:25]([C:27]1[S:44][C:30]2[C:31]3[CH:39]=[CH:38][C:37]([C:40](=[O:43])[NH:41][CH3:42])=[CH:36][C:32]=3[O:33][CH2:34][CH2:35][C:29]=2[CH:28]=1)=[O:26]>CCOC(C)=O>[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[O:8])=[CH:5][C:4]=1[N:24]([CH3:45])[C:25]([C:27]1[S:44][C:30]2[C:31]3[CH:39]=[CH:38][C:37]([C:40]([NH:41][CH3:42])=[O:43])=[CH:36][C:32]=3[O:33][CH2:34][CH2:35][C:29]=2[CH:28]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58204175HCID 58204175, compound

Product 1

HCID 58204057N2-(2-chloro-5-(piperazine-1-carbonyl)phenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of HCl in EtOAc (4M, 20 mL) was slowly added into a solution of tert-butyl 4-(4-chloro-3-(N-methyl-8-(methylcarbamoyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)benzoyl)piperazine-1-carboxylate (390 mg, 0.61 mmol) in EtOAc (5 mL) at 0° C. The mixture was stirred at room temperature for overnight. The solids were filtered and washed with EtOAc, dried to give 333 (250 mg, yield 71%). 1H NMR (MeOD, 400 MHz): δ7.76-7.42 (m, 7H, ArH, NH), 6.90 (s, 1H, ═CH), 4.23-2.89 (m, 19H). LC-MS: (ESI, m/z)=539 [M+H]+, 561 [M+Na]+

Workup

  1. filtrationThe solids were filtered
  2. washwashed with EtOAc
  3. customdried

Sources & evidence

ORD record
ord-3a02914532014457865c9b4924cee88b
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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