Dicyclohexylcarbodiimide → 3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[1-oxo-2-(1,1-dioxothiomorpholin-4-yl)ethylamino]phenyl]benzo[b]thiophene

HRID 1070349Notes

Reaction equation

HRID 1070349 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:32]=[S:33]1(=[O:43])[CH2:38][CH2:37][N:36]([CH2:39][C:40](O)=[O:41])[CH2:35][CH2:34]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.[Cl-].[Na+].O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:15]4[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=4[S:17][C:18]=3[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:40](=[O:41])[CH2:39][N:36]4[CH2:37][CH2:38][S:33](=[O:43])(=[O:32])[CH2:34][CH2:35]4)=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 28062362-(1,1-Dioxo-1lambda6-thiomorpholin-4-yl)acetic acidHCID 224627922-(4-Aminophenyl)-3-[4-(2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Product 1

HCID 211830213-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-[1-oxo-2-(1,1-dioxothiomorpholin-4-yl)ethylamino]phenyl]benzo[b]thiopheneYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-(4-aminophenyl)benzo[b]thiophene (50 mg) and (1,1-dioxothiomorpholin-4-yl)acetic acid (30 mg) were dissolved in DMF (2.0 mL), treated with DCC (30 mg) and HOAt (28 mg) sequentially, and allowed to stir at ambient temperature under argon for 19 h. The reaction mixture was diluted with brine (30 mL), extracted with ethyl acetate (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound (65 mg).

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e9fea735215647588b021fab1153128c
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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