Sulfuric Acid → 3-(3-(4-(Pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine hemisulfate

HRID 557281Notes

Reaction equation

HRID 557281 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.[S:28](=[O:32])(=[O:31])([OH:30])[OH:29]>CO>[S:28]([OH:32])([OH:31])(=[O:30])=[O:29].[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.[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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 16719049E-1210

Product 1

HCID 1317292783-(3-(4-(Pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine hemisulfate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (1 g) was added methanol (4 mL). While heating and stirring at 40° C, to this suspension was added a solution of concentrated sulfuric acid (79.4 μL) in methanol (1 mL) dropwise, which turned into a solution. After stirring at 40° C for 10 minutes and seeding, crystals precipitated. After stirring at 40° C for 20 minutes, tert-butyl methyl ether (25 mL) was added dropwise at the same temperature for one hour, followed by slow cooling, then stirring at 23° C for three hours. The precipitated crystals were filtered and dried to obtain the title compound (1.04 g).

Workup

  1. temperatureWhile heating
  2. stirringAfter stirring at 40° C for 10 minutes
  3. customseeding, crystals precipitated
  4. stirringAfter stirring at 40° C for 20 minutes
  5. additiontert-butyl methyl ether (25 mL) was added dropwise at the same temperature for one hour
  6. stirringstirring at 23° C for three hours
  7. filtrationThe precipitated crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-c5e626bac43e4a4f949568cc5dfa541e
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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