Tetrahydrofuran → HCID 178462566, compound

HRID 641012Notes

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.[NH2:50][C:51]1[CH:56]=[CH:55][C:54]([CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])=[CH:53][CH:52]=1>CCOC(C)=O.CCCCCC>[Cl:41][C:40]1[C:36]([C:34]([NH:33][C:29]2[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=2)[C:25]([C:21]2[CH:20]=[C:19]3[C:24]([C:16](=[CH:15][NH:50][C:51]4[CH:52]=[CH:53][C:54]([CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])=[CH:55][CH:56]=4)[C:17](=[O:44])[NH:18]3)=[CH:23][CH:22]=2)=[O:26])=[O:35])=[N:37][N:38]([CH2:42][CH3:43])[CH:39]=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-(4-Amino-phenyl)-butyric acid (41.4 mg, 0.231 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 45% yield (0.061 g, 0.102 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-7b7a599362b940e1b62d804111c2fb65
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692005B2

Reaction notes

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