Citric Acid → HCID 25070440, compound

HRID 557291Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1.[C:28]([OH:40])(=[O:39])[CH2:29][C:30]([CH2:35][C:36]([OH:38])=[O:37])([C:32]([OH:34])=[O:33])[OH:31].CO>COC(C)(C)C>[C:28]([OH:40])(=[O:39])[CH2:29][C:30]([CH2:35][C:36]([OH:38])=[O:37])([C:32]([OH:34])=[O:33])[OH:31].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 32.5 °C

Procedure

To 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-yl amine (1 g) and citric acid (564 mg) was added methanol (3 mL), and the suspension was stirred at 30 to 35° C, to turn it into a solution. Under stirring at 30° C, after adding tert-butyl methyl ether (3 mL) dropwise over 15 minutes to this solution and seeding, crystals precipitated. After stirring at 30° C for 10 minutes, tert-butyl methyl ether (15 mL) was added at the same temperature for one hour, and after slow cooling, mixture was stirred at 23° C for two hours. The precipitated crystals were filtered and dried to obtain the title compound (1.34 g) as a white crystal.

Workup

stirringUnder stirring at 30° C
customprecipitated
stirringAfter stirring at 30° C for 10 minutes
additiontert-butyl methyl ether (15 mL) was added at the same temperature for one hour
stirringafter slow cooling, mixture was stirred at 23° C for two hours
filtrationThe precipitated crystals were filtered
customdried

Sources & evidence

ORD record: ord-6016b34a1d3f420987ce5153f8c27450
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058444B2

Reaction notes

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