Tetrahydrofuran → 3-[4-[[6-[3-[(5-chloro-1-methylpyrazole-4-carbonyl)amino]benzoyl]-2-oxo-1H-indol-3-ylidene]methylamino]phenyl]propanoic acid

HRID 2352971Notes

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

Participants

Conditions

Temperature: 65 °C

Procedure

A small screw cap test tube was charged with 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 328, 100 mg, 0.2365 mmol) and THF (2.5 mL). To the resulting solution was added 3-(4-Amino-phenyl)-propionic acid (39.1 mg, 0.237 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 (˜50 mL). The precipitate that formed was collected by filtration and washed with acetone (˜15 mL) to afford the title compound in 57% yield (0.077 g, 0.1351 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 (˜15 mL)

Sources & evidence

ORD record: ord-4df38ec5c94246de9491b81af6aa8c62
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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