Succinic anhydride → HCID 19808337, compound

HRID 373860Notes

Reaction equation

[C:1]([CH:3]([C:13]([C:15]1[C:16]2[CH2:29][S:28][C:27]3[C:30]([CH2:34][OH:35])=[CH:31][CH:32]=[CH:33][C:26]=3[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:36]1(=[O:42])[O:41][C:39](=[O:40])[CH2:38][CH2:37]1>N1C=CC=CC=1>[C:39]([CH2:38][CH2:37][C:36]([O:35][CH2:34][C:30]1[C:27]2[S:28][CH2:29][C:16]3[C:15]([C:13](=[O:14])[CH:3]([C:1]#[N:2])[C:4]([NH:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[O:5])=[N:19][N:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17]=3[C:26]=2[CH:33]=[CH:32][CH:31]=1)=[O:42])([OH:41])=[O:40]

Participants

Conditions

Temperature: 45 °C

Procedure

2-Cyano-3-(1,4-dihydro-6-hydroxymethyl-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide (1.2 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 0.95 g of 3-[6-(3-carboxy-propanoyloxymethyl)-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-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-2052396001b54906b83ecc59ba577cdf
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166152

Reaction notes

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