Hydrochloric Acid → HCID 25052790, compound

HRID 557276Notes

Reaction equation

HRID 557276 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.[ClH:28].COC(C)(C)C>CO>[ClH:28].[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 16719049E-1210

Product 1

HCID 25052790HCID 25052790, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (500 mg) in methanol (2 mL) was added concentrated hydrochloric acid (123 μL) dropwise at 25° C, and the suspension turned into a solution. After adding tert-butyl methyl ether (2 mL) dropwise for 20 minutes at the same temperature and seeding, crystals precipitated. After stirring at 25° C for 10 minutes, tert-butyl methyl ether (6 mL) was added dropwise for 30 minutes, and the mixture was stirred at the same temperature for two hours. The precipitated crystals were filtered and dried to obtain the title compound (513 mg) as a white crystal.

Workup

  1. customprecipitated
  2. additiontert-butyl methyl ether (6 mL) was added dropwise for 30 minutes
  3. stirringthe mixture was stirred at the same temperature for two hours
  4. filtrationThe precipitated crystals were filtered
  5. customdried

Sources & evidence

ORD record
ord-b12443b0186f44b893fe8753e199f44b
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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