Benzenamine, 4-(4-morpholinyl)- → HCID 178463067, compound

HRID 2352754Notes

Reaction equation

O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH2:29][CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:10]=2)[NH:5][C:4]1=[O:31].[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1>C1COCC1>[N:39]1([C:36]2[CH:35]=[CH:34][C:33]([NH:32][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[N:24]([CH2:29][CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=6)=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])[CH:10]=4)[NH:5][C:4]3=[O:31])=[CH:38][CH:37]=2)[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (prepared below, 30 mg, 0.072 mmol) and THF (1 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (19.3 mg, 0.1082 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature, concentrated in vacuo and redissolved in EtOAc. Hexanes were added to the reaction mixture. The solid precipitate that formed was filtered and washed with ˜1 mL of ice cold THF yielding 36% (15 mg, 0.026 mmol) of the title compound.

Workup

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionredissolved in EtOAc
additionHexanes were added to the reaction mixture
customThe solid precipitate that formed
filtrationwas filtered

Sources & evidence

ORD record: ord-9031f7737705494fbbe9995e131b687f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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