Benzenamine, 4-(4-morpholinyl)- → HCID 178517288, compound

HRID 640895Notes

Reaction equation

HRID 640895 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:28].[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>C1COCC1>[N:36]1([C:33]2[CH:32]=[CH:31][C:30]([NH:29][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[S:24][CH:25]=[CH:26][CH:27]=6)=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:28])=[CH:35][CH:34]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 178517289N-[3-[3-(hydroxymethylidene)-2-oxo-1H-indole-6-carbonyl]phenyl]thiophene-2-carboxamide

Product 1

HCID 178517288HCID 178517288, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 45, 100 mg, 0.256 mmol) and THF (2 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (55 mg, 0.3086 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The solid residue was recrystallized with ˜5 mL of i-prOH affording the title compound in 82% yield (0.116 g, 0.2107 mmol).

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe solid residue was recrystallized with ˜5 mL

Sources & evidence

ORD record
ord-2996e63dc2764bbf9f6dd84ed31fef16
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

Loading…