Triethylamine → Methyl 4-[3-(4-{[(2-{[3-(chlorosulfonyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)propyl]benzoate

HRID 926026Notes

Reaction equation

HRID 926026 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:32][CH2:31][CH2:30][CH2:29][C:5]=2[C:6]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)=[O:8].C(N(CC)CC)C.[Cl:40][S:41]([C:44]1[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47](Cl)=[O:48])(=[O:43])=[O:42]>ClCCl>[Cl:40][S:41]([C:44]1[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47]([NH:1][C:2]1[S:3][C:4]2[CH2:32][CH2:31][CH2:30][CH2:29][C:5]=2[C:6]=1[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)=[CH:14][CH:15]=1)=[O:8])=[O:48])(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 68207877Methyl 4-[3-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)propyl]benzoate

Product 1

HCID 86676333Methyl 4-[3-(4-{[(2-{[3-(chlorosulfonyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)propyl]benzoateYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3.34 g of methyl 4-[3-(4-{[(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)propyl]benzoate, 2.2 mL of triethylamine, and 40 mL of dichloromethane were added a mixture of 2.2 g of 3-(chlorosulfonyl)benzoyl chloride and 10 mL of dichloromethane under ice-cooling, followed by stirring at room temperature for 7 hours. The reaction mixture was concentrated under reduced pressure and the residue was suspended in ethanol. The precipitate was collected by filtration to obtain 1.42 g of methyl 4-[3-(4-{[(2-{[3-(chlorosulfonyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)propyl]benzoate as a yellow solid.

Workup

  1. additionwere added
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-03b5a62b1af9412880ea684d97a79ce3
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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