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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 1470131
Notes
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Reaction equation

HRID 1470131 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-bb4880ed6cb64137afb7bd51b851a7b8
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006281B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes