Dichloromethane → HCID 178510989, compound

HRID 732848Notes

Reaction equation

HRID 732848 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)/[C:6](=[C:13](/OCC)\[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:5]1=[O:23])(=[O:3])C.C(OC(=O)[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)(C)(C)C.ClCCl>CN(C=O)C.CO>[OH-:3].[NH4+:4].[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH:45]/[C:13](=[C:6]2\[C:5](=[O:23])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[CH:10][CH:11]=3)/[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:41][CH:40]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 11045014HCID 11045014, compoundHCID 58720810Carbamic acid, [6-[(4-aminobenzoyl)amino]hexyl]-, 1,1-dimethylethyl ester

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 178510989HCID 178510989, compoundYield 162%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

1-Acetyl-3-[1-ethoxy-1-phenyl-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one (50 mg, 0.163 mmol) and [6-(4-amino-benzoylamino)-hexyl]-carbamic acid tert-butyl ester (65 mg, 0.195 mmol) were combined in DMF (1 mL) and stirred for 24 hours at 110° C. The DMF was removed by rotary evaporation under high vacuum. The residue was re-dissovled in MeOH (1 mL), a solution of 0.5 M sodium methoxide was added (0.5 mL) and the reaction was stirred at ambient temperature for 1 hour. 4N HCl in dioxane(1 mL) was added and the reaction was stirred overnight. The reaction was concentrated by rotary evaporation. Flash chromatography in a polar gradient of [20%(10% ammonium hydroxide in MeOH) and 80% dichloromethane] provided 60 mg of N-(6-amino-hexyl)-4-({[2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-phenyl-methyl}-amino)-benzamide (82% yield).

Workup

  1. customThe DMF was removed by rotary evaporation under high vacuum
  2. additiona solution of 0.5 M sodium methoxide was added (0.5 mL)
  3. stirringthe reaction was stirred at ambient temperature for 1 hour
  4. addition4N HCl in dioxane(1 mL) was added
  5. stirringthe reaction was stirred overnight
  6. concentrationThe reaction was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-ba8e41a433e84f37b537274615461d9b
Source dataset
uspto-grants-2009_09
Patent number
US07588899B2

Reaction notes

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