Efatutazone Dihydrochloride → Hydrochloric Acid

HRID 883085Notes

Reaction equation

[ClH:1].Cl.[NH2:3][C:4]1[C:36]([CH3:37])=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][C:5]=1[CH3:38]>O>[NH2:3][C:4]1[C:5]([CH3:38])=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[CH:21][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:31][CH:32]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:35][C:36]=1[CH3:37].[ClH:1]

Participants

Conditions

Temperature: 0 °C

Procedure

2.0 g of the monohydrate of 5-(4-{[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1-H-benzimidazol-2-yl]methoxy}benzyl)-1,3-thiazolidine-2,4-dione dihydrochloride obtained by a method similar to the method described in Example 1-1 was suspended in 100 ml of water. The resulting suspension was refluxed for 2 hours. The reaction mixture was cooled to 0° C. and agitated for 1 hour. The obtained crystalline form was filtered off and rinsed with water. The obtained moist crystalline form was dried for 14 hours at a pressure of approximately 80 kPa and at 50° C. to give a crystalline form, wherein the proportion Of 5-(4-{[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1-H-benzimidazol-2-yl]methoxy}benzyl)-1,3-thiazolidine-2,4-dione and hydrochloric acid was approximately 1 to 1.1.

Workup

temperatureThe resulting suspension was refluxed for 2 hours
filtrationThe obtained crystalline form was filtered off
washrinsed with water
customThe obtained moist crystalline form was dried for 14 hours at a pressure of approximately 80 kPa and at 50° C.

Sources & evidence

ORD record: ord-cf63d66a67da4449b09a3879927dfd79
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236834B2

Reaction notes

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