Dimethylformamide → HCID 90370232, compound

HRID 2175992Notes

Reaction equation

HRID 2175992 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:38][CH2:37][CH2:36][CH2:35][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)=[O:15])=[O:7].[CH3:42][CH2:43][CH:44]([NH2:47])[CH2:45][CH3:46].C(N(C(C)C)C(C)C)C.CN(C=O)C>O.C(OCC)(=O)C>[CH3:42][CH2:43][CH:44]([NH:47][CH2:2][C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:38][CH2:37][CH2:36][CH2:35][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)=[O:15])=[O:7])[CH2:45][CH3:46]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 90370193HCID 90370193, compound

Product 1

HCID 90370232HCID 90370232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8.00 g of methyl 4-[2-(4-{[(2-{[3-(chloromethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, 4.8 mL of pentan-3-amine, 3.5 mL of N-ethyl-N-isopropylpropan-2-amine, and 80 mL of DMF was stirred for 13 hours at 80° C. Ethyl acetate and water were added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (2% methanol/chloroform), thereby obtaining 6.57 g of methyl 4-{2-[4-({[2-({3-[(pentan-3-ylamino)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 sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (2% methanol/chloroform)

Sources & evidence

ORD record
ord-ea78eb27c535405789ecee6a12de4974
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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