Pyridine → 1,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 1668572Notes

Reaction equation

HRID 1668572 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].CN(C1C=CC=CN=1)C.[NH2:21][C:22]1[C:39]([OH:40])=[CH:38][C:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30][C:24]=2[CH:23]=1>C(Cl)Cl>[OH:40][C:39]1[C:22]([NH:21][S:8]([CH3:7])(=[O:10])=[O:9])=[CH:23][C:24]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH2:26][C:25]=2[CH:38]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 591504721,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Product 1

HCID 591504841,1-dimethylethyl 7-hydroxy-8-[(methylsulfonyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.17 ml), methanesulfonyl chloride (0.16 ml) and dimethylaminopyridine (catalytic quantity) were added at 0° C. to a solution in DCM (10 ml) of 1,1-dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (0.5 g). The solution was stirred at room temperature overnight. Volatiles were evaporated under reduced pressure and the residue was partitioned between aqueous NaHCO3 and DCM. The organic layer was concentrated and submitted to column chromatography to provide the title compound (0.53 g) as a yellow oil. MS (m/z): 357 [MH]+.

Workup

  1. customVolatiles were evaporated under reduced pressure
  2. customthe residue was partitioned between aqueous NaHCO3 and DCM
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f4326cfd679f4503bd634a52253cfca9
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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