HCID 641343, compound → HCID 86713256, compound

HRID 927999Notes

Reaction equation

HRID 927999 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11].Cl[S:20]([C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26])(=[O:22])=[O:21].[NH2:32][C:33]1[C:42]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[C:41]2[C:36]([CH:37]3[CH2:50][CH:38]3[CH2:39][O:40]2)=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:4]=1[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][N:10]([CH3:11])[CH3:12])[C:25]([C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[S:20]([NH:32][C:33]1[C:42]([C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[C:41]2[C:36]([CH:37]3[CH2:50][CH:38]3[CH2:39][O:40]2)=[CH:35][CH:34]=1)(=[O:22])=[O:21])=[O:26]

Participants

5

Reactant 3

HCID 641343HCID 641343, compound2×HCID 4718975HCID 4718975, compound2×HCID 86713328HCID 86713328, compound2×

Product 1

HCID 86713256HCID 86713256, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)amine (Intermediate 120, 0.179 g) in DCM (2 mL) was added dropwise with stirring to a cooled solution of 2-chlorosulfonylbenzoyl chloride (Intermediate 121, 0.17 g) in DCM (20 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour then a solution of tert-butyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (Intermediate 122, 0.185 g) in DCM (2 mL) was added. The resultant mixture was stirred and heated at 30-35° C. overnight. After cooling, the mixture was concentrated under vacuum and the residue was purified by HPLC (C18) to give tert-butyl (1aRS,7bSR)-5-{2-[N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)carbamoyl]-benzenesulfonylamino}-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (0.03 g) as a yellow oil.

Workup

  1. temperatureheated at 30-35° C. overnight
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under vacuum
  4. customthe residue was purified by HPLC (C18)

Sources & evidence

ORD record
ord-5f001e802cfe4a9fb50bc545f3f9cc46
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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