tert-Butyl methyl ether → 3-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid(4-methoxy-4'-sulfamoyl-biphenyl-3-ylmethyl)-(4-methylamino-cyclohexyl)-amide hydrochloride

HRID 2389687Notes

Reaction equation

HRID 2389687 reaction equation
[Cl:1][C:2]1[C:3]2[C:47]([F:48])=[CH:46][CH:45]=[C:44]([F:49])[C:4]=2[S:5][C:6]=1[C:7]([N:9]([CH2:25][C:26]1[CH:27]=[C:28]([C:34]2[CH:39]=[CH:38][C:37]([S:40](=[O:43])(=[O:42])[NH2:41])=[CH:36][CH:35]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:10]1[CH2:15][CH2:14][CH:13]([N:16](C)[C:17](=O)OC(C)(C)C)[CH2:12][CH2:11]1)=[O:8].CC(OC)(C)C>C(Cl)Cl>[ClH:1].[CH3:33][O:32][C:31]1[CH:30]=[CH:29][C:28]([C:34]2[CH:39]=[CH:38][C:37]([S:40](=[O:43])(=[O:42])[NH2:41])=[CH:36][CH:35]=2)=[CH:27][C:26]=1[CH2:25][N:9]([CH:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH3:17])[CH2:12][CH2:11]1)[C:7]([C:6]1[S:5][C:4]2[C:44]([F:49])=[CH:45][CH:46]=[C:47]([F:48])[C:3]=2[C:2]=1[Cl:1])=[O:8]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 59683633tert-Butyl {4-[(3-chloro-4,7-difluoro-benzo[b]thiophene-2-carbonyl)-(4-methoxy-4'-sulfamoyl-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 683137003-Chloro-4,7-difluoro-benzo[b]thiophene-2-carboxylic acid(4-methoxy-4'-sulfamoyl-biphenyl-3-ylmethyl)-(4-methylamino-cyclohexyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl carbamate 217 (100 mg, 0.14 mmol) is deprotected using Method F. The isolated salt is then dissolved in the minimum amount of DCM and added dropwise to cold (0° C.) TBME (25 mL). The resultant pale yellow precipitate is isolated by filtration, washed with TBME (10 mL) and diethyl ether (10 mL) and dried to afford the title compound.

Workup

  1. customThe resultant pale yellow precipitate is isolated by filtration
  2. washwashed with TBME (10 mL) and diethyl ether (10 mL)
  3. customdried

Sources & evidence

ORD record
ord-a098537381bc49ce949a4fdd70e214d0
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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