1-Propanesulfonyl chloride → tert-Butyl 7-{[(propylsulfonyl)amino]methyl}-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 242110Notes

Reaction equation

HRID 242110 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:10]2[C:13]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[CH2:30]([S:33](Cl)(=[O:35])=[O:34])[CH2:31][CH3:32]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:30]([S:33]([NH:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:10]2[C:13]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:14][CH2:15][CH2:16]2)=[CH:5][CH:4]=1)(=[O:35])=[O:34])[CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 58246415tert-Butyl 7-(aminomethyl)-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86653008tert-Butyl 7-{[(propylsulfonyl)amino]methyl}-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 7-(aminomethyl)-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (33 mg, 0.084 mmol) was dissolved in dichloromethane. 4-Dimethylaminopyridine (30.7 mg, 0.252 mmol) was added. After stirring for 5 min propane-1-sulfonyl chloride (12 mg, 0.084 mmol) was added and stirring was continued over night. The reaction mixture was diluted with dichloromethane (30 ml) and washed with aqueous ammonium chloride solution. The organic layer was washed with water, dried (MgSO4) and concentrated in vacuo. The crude product was used for the next step without further purification. Yield: 37 mg.

Workup

  1. additionwas added
  2. waitwas continued over night
  3. washwashed with aqueous ammonium chloride solution
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-167c1cd75b9742cd8803f51eba73346c
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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