Tetrahydrofuran → HCID 178462567, compound

HRID 641013

Reaction equation

CN1CCN(C2C=CC(N[CH:15]=[C:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]([C:27]5[CH:28]=[C:29]([NH:33][C:34]([C:36]6[C:40]([Cl:41])=[CH:39][N:38]([CH2:42][CH3:43])[N:37]=6)=[O:35])[CH:30]=[CH:31][CH:32]=5)=[O:26])=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:44])=CC=2)CC1.C1COCC1.[N:50]1([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[CH:58][CH:57]=2)[CH2:54][CH2:53][CH2:52][CH2:51]1>CCOC(C)=O.CCCCCC>[O:44]=[C:17]1[C:16](=[CH:15][NH:62][C:59]2[CH:58]=[CH:57][C:56]([CH2:55][N:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:61][CH:60]=2)[C:24]2[C:19](=[CH:20][C:21]([C:25]([C:27]3[CH:28]=[C:29]([NH:33][C:34]([C:36]4[C:40]([Cl:41])=[CH:39][N:38]([CH2:42][CH3:43])[N:37]=4)=[O:35])[CH:30]=[CH:31][CH:32]=3)=[O:26])=[CH:22][CH:23]=2)[NH:18]1

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 4-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid [3-(3-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 342, 100 mg, 0.229 mmol) and THF (2.5 mL). To the resulting solution was added 4-Pyrrolidin-1-ylmethyl-phenylamine (40.3 mg, 0.229 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 solid that precipitated was collected by filtration and washed with 0° C. acetone (˜10 mL) affording the title compound in 31% yield (0.043 g, 0.072 mmol).

Workup

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
customThe solid that precipitated
filtrationwas collected by filtration
washwashed with 0° C. acetone (˜10 mL)

Sources & evidence

ORD record: ord-0e1a3aac72fe428889a9fc139efcfd88
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692005B2

Linked notes

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