Tetrahydrofuran → HCID 178424289, compound

HRID 2352977Notes

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](=[O:29])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].C1COCC1.[N:36]1([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1>CCOC(C)=O.CCCCCC>[CH3:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]([NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:3](=[CH:2][NH:48][C:45]4[CH:44]=[CH:43][C:42]([CH2:41][N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)=[CH:47][CH:46]=4)[C:4](=[O:30])[NH:5]3)=[CH:10][CH:9]=2)=[O:13])[CH:15]=1)=[O:29]

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with N-[3-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-2-methyl-benzamide (prepared below, 100 mg, 0.251 mmol) and THF (2.5 mL). To the resulting solution was added 4-Pyrrolidin-1-ylmethyl-phenylamine (44.2 mg, 0.251 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and diluted with EtOAc (˜5 mL) and Hexane (˜40 mL). The precipitate that formed was collected by filtration and washed with acetone (˜5 mL) to afford the title compound in 56% yield (0.078 g, 0.1401 mmol).

Workup

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
customThe precipitate that formed
filtrationwas collected by filtration
washwashed with acetone (˜5 mL)

Sources & evidence

ORD record: ord-a906f55ddf084b42afddc80d5a3a38cc
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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