1-(4-Amino-phenoxy)-3-diethylaminopropan-2-ol → HCID 178464105, compound

HRID 2352873Notes

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[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[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:30].[NH2:31][C:32]1[CH:47]=[CH:46][C:35]([O:36][CH2:37][CH:38]([OH:45])[CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])=[CH:34][CH:33]=1>C1COCC1>[CH2:43]([N:40]([CH2:41][CH3:42])[CH2:39][CH:38]([OH:45])[CH2:37][O:36][C:35]1[CH:34]=[CH:33][C:32]([NH:31][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:15]=[C:16]([NH:20][C:21]([C:23]5[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])[CH:17]=[CH:18][CH:19]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:30])=[CH:47][CH:46]=1)[CH3:44]

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 132.3 mg, 0.3288 mmol) and THF (2 mL). To the resulting solution was added 1-(4-Amino-phenoxy)-3-diethylamino-propan-2-ol (prepared below; 95.7 mg, 0.4015 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was recrystallized from EtOAc (5 mL) and Hexanes (2 mL) yielding the title compound in 35% yield (0.072 g, 0.1156 mmol).

Workup

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
customThe room temperature reaction mixture
concentrationwas concentrated in vacuo
customThe solid residue was recrystallized from EtOAc (5 mL) and Hexanes (2 mL)

Sources & evidence

ORD record: ord-cf5c3d1d9a2d483da64c131d95e7ce54
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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