Dimethylformamide → HCID 90370146, compound

HRID 2176009Notes

Reaction equation

HRID 2176009 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:8][C:9]1[CH:10]=[C:11]([CH:45]=[CH:46][CH:47]=1)[C:12]([NH:14][C:15]1[S:16][C:17]2[CH2:44][CH2:43][CH2:42][CH2:41][C:18]=2[C:19]=1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)=[O:21])=[O:13])[CH:5]1[CH2:7][CH2:6]1.Br[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:5]1([N:4]([CH2:8][C:9]2[CH:10]=[C:11]([CH:45]=[CH:46][CH:47]=2)[C:12]([NH:14][C:15]2[S:16][C:17]3[CH2:44][CH2:43][CH2:42][CH2:41][C:18]=3[C:19]=2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=3)=[CH:25][CH:24]=2)=[O:21])=[O:13])[CH2:3][CH2:2][NH:1][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 90370332HCID 90370332, compound

Product 1

HCID 90370146HCID 90370146, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g of methyl 4-(2-{4-[({2-[(3-{[(2-aminoethyl)(cyclopropyl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate, 0.20 mL of ethyl bromoacetate, 212 mg of potassium carbonate, and 20 mL of DMF was stirred overnight at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography, thereby obtaining 140 mg of methyl 4-{2-[4-({[2-({3-[(cyclopropyl {2-[(2-ethoxy-2-oxoethyl)amino]ethyl}amino)methyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-90f8926e926c4cce9e29118cd065166e
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

Loading…