N-(benzo[1,3]dioxol-5-ylmethyl)-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide → Methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylcarbamoyl}cyclohexanecarboxylate

HRID 1856840Notes

Reaction equation

HRID 1856840 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[C:15]4[CH2:23][CH2:22][CH2:21][CH2:20][C:16]=4[S:17][C:18]=3[NH2:19])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:24][O:25][C:26]([CH:28]1[CH2:33][CH2:32][CH:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]1)=[O:27]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[C:15]4[CH2:23][CH2:22][CH2:21][CH2:20][C:16]=4[S:17][C:18]=3[NH:19][C:34]([CH:31]3[CH2:30][CH2:29][CH:28]([C:26]([O:25][CH3:24])=[O:27])[CH2:33][CH2:32]3)=[O:35])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 11782481N-(benzo[1,3]dioxol-5-ylmethyl)-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 15380636Methyl 4-(chlorocarbonyl)cyclohexane-1-carboxylate

Product 1

HCID 15380637Methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylcarbamoyl}cyclohexanecarboxylate

Procedure

Analogously to Example 1, the reaction of N-(benzo[1,3]dioxol-5-ylmethyl)-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide with 4-methoxycarbonylcyclohexanecarbonyl chloride ("B") gives the compound methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylcarbamoyl}cyclohexanecarboxylate, m.p. 173°.

Sources & evidence

ORD record
ord-245f597757d0494b944fa386756496b4
Source dataset
uspto-grants-2000_11
Patent number
US06143777

Reaction notes

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