Acetone → HCID 54767922, compound

HRID 472771Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH2:34][OH:35])[CH:32]=2)=[CH:4][N:3]=1.CC(C)=O.[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43]>O>[C:40]([OH:52])(=[O:51])[CH2:41][C:42]([CH2:47][C:48]([OH:50])=[O:49])([C:44]([OH:46])=[O:45])[OH:43].[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=4)=[O:19])=[CH:15][CH:16]=3)=[CH:9][S:10][C:6]=2[C:5]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH2:34][OH:35])[CH:32]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

N-(4-{4-amino-7-[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]thieno[3,2-c]pyridin-3-yl}phenyl)-N′-(3-fluorophenyl)urea free base solids (398.06 mg) was added to 20 mL of acetone:water mixture (75:25 v:v) and heated with stirring at 70° C. for 30 minutes. The sample remained as a suspension. Citric acid (1.2 mL, 1 M) solution in water was added with continued stirring at 70° C. After adding the citric acid solution, slight more of the solid was observed to dissolve. Within 12 minutes after the addition of citric acid, a suspension was formed. The suspension was stirred at 70° C. for approximately one hour. The solid was isolated by vacuum filtration.

Workup

stirringwith continued stirring at 70° C
dissolutionto dissolve
customa suspension was formed
stirringThe suspension was stirred at 70° C. for approximately one hour
customThe solid was isolated by vacuum filtration

Sources & evidence

ORD record: ord-f41819351e074858ad19a2f20b0ca846
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633217B2

Reaction notes

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