Dimethylformamide → N,N'-(13-oxo-3,6,9,17,20,23-hexaoxa-12,14-diazapentacosane-1,25-diyl)bis[4-(2,6-difluoro-4-(2-carboethoxypropenyl)phenoxy)benzenesulfonamide]

HRID 1479396

Reaction equation

HRID 1479396 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:39]=[CH:38][C:20]([O:21][C:22]2[C:27]([F:28])=[CH:26][C:25](/[CH:29]=[C:30](\[CH3:36])/[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:24][C:23]=2[F:37])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[CH3:40][N:41]([CH:43]=[O:44])C>>[O:44]=[C:43]([NH:41][CH2:40][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([O:21][C:22]2[C:23]([F:37])=[CH:24][C:25]([CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:36])=[CH:26][C:27]=2[F:28])=[CH:38][CH:39]=1)(=[O:16])=[O:15])[NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:39]=[CH:38][C:20]([O:21][C:22]2[C:23]([F:37])=[CH:24][C:25]([CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:36])=[CH:26][C:27]=2[F:28])=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 70906018(E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate2×

Product 1

HCID 86672340N,N'-(13-oxo-3,6,9,17,20,23-hexaoxa-12,14-diazapentacosane-1,25-diyl)bis[4-(2,6-difluoro-4-(2-carboethoxypropenyl)phenoxy)benzenesulfonamide]

Procedure

Carbonyldiimidisole (16.2 mg, 0.10 mmol) was added to a solution of (E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate (intermediate 44.2) (125 mg, 0.22 mmol) in DMF (2 mL) and stirred for 23 hours at which time the solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water (4×10 mL), dried (Na2SO4) and concentrated to give the title compound (132 mg).

Workup

  1. customwas removed under vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water (4×10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31d801a4d1ca43e0ae64da039d6f48c3
Source dataset
uspto-grants-2016_08
Patent number
US09408840B2

Linked notes

Loading…