Dimethylamine, hydrochloride → N2-(2,4-dichlorophenyl)-N2,N9,N9-trimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,9-dicarboxamide

HRID 84575Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:29])[C:10]([C:12]1[S:21][C:20]2[C:19]3[CH:22]=[C:23]([C:26](O)=[O:27])[CH:24]=[CH:25][C:18]=3[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=1)=[O:11].Cl.[CH3:31][NH:32][CH3:33]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:29])[C:10]([C:12]1[S:21][C:20]2[C:19]3[CH:22]=[C:23]([C:26]([N:32]([CH3:33])[CH3:31])=[O:27])[CH:24]=[CH:25][C:18]=3[O:17][CH2:16][CH2:15][C:14]=2[CH:13]=1)=[O:11]

Participants

Reactant 2

HCID 10473Dimethylamine, hydrochloride

HCID 668689222-[(2,4-Dichloro-phenyl)-methyl-carbamoyl]-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carboxylic acid

Product 1

HCID 57900154N2-(2,4-dichlorophenyl)-N2,N9,N9-trimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,9-dicarboxamide

Procedure

2-[(2,4-Dichloro-phenyl)-methyl-carbamoyl]-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carboxylic acid and dimethylamine hydrochloride salt were reacted in the general amide coupling procedure to give 288. NMR: (CDCl3): 2.73-3.04 (6 H, br m), 2.95-3.00 (2 H, m), 3.29 (3 H, s, Me), 4.17-4.20 (2 H, m), 6.79 (1 H, s, Ar), 6.93 (1 H, d, J 8.3, Ar), 7.19-7.29 (3 H, m, Ar) and 7.47-7.48 (2 H, m, Ar). MS: (ESI+) MH+=475.04

Sources & evidence

ORD record: ord-a06a094cb5c24578a8a2a699c54d5964
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846762B2

Reaction notes

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