Succinic anhydride → 3-[5-(3-carboxy-propanoyloxymethyl)-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl]-2-cyano-3-oxo-N-phenyl-propanamide

HRID 21551Notes

Reaction equation

[C:1]([CH:3]([C:13]([C:15]1[C:16]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][C:30]=3[CH2:33][OH:34])[C:17]=2[N:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:19]=1)=[O:14])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].[C:35]1(=[O:41])[O:40][C:38](=[O:39])[CH2:37][CH2:36]1>N1C=CC=CC=1>[C:38]([CH2:37][CH2:36][C:35]([O:34][CH2:33][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH2:32][C:16]1[C:15]([C:13](=[O:14])[CH:3]([C:1]#[N:2])[C:4]([NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[O:5])=[N:19][N:18]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:17]=12)=[O:41])([OH:40])=[O:39]

Participants

Conditions

Temperature: 45 °C

Procedure

2-cyano-3-(1,4-dihydro-5-hydroxymethyl-1-phenyl-indeno [1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide (1.1 g) is reacted with succinic anhydride (0.8 g) in anhydrous pyridine (40 ml) under stirring at 45° C. for 20 hours. After cooling the reaction mixture is diluted in ice water and the precipitate is filtered and washed with water. Crystallization from CH2Cl2 /isopropanol yields 0.85 g of 3-[5-(3-carboxy-propanoyloxymethyl) -1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl]-2-cyano-3-oxo-N-phenyl-propanamide.

Workup

temperatureAfter cooling the reaction mixture
filtrationthe precipitate is filtered
washwashed with water
customCrystallization from CH2Cl2 /isopropanol

Sources & evidence

ORD record: ord-a384f5df2ba74b14bc1c12c64da1c034
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424308

Reaction notes

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