Methanesulfonic Acid → HCID 25070763, compound

HRID 557283Notes

Reaction equation

HRID 557283 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.[CH3:28][S:29]([OH:32])(=[O:31])=[O:30]>CO>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[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 6395Methanesulfonic AcidHCID 16719049E-1210

Product 1

HCID 25070763HCID 25070763, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

To 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-yl amine (500 mg) was added methanol (1.5 mL), and under heat-stirring at 40° C, to this suspension was added a solution of methanesulfonic acid (96.5 μL) in methanol (0.5 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 (10 mL) was added thereto dropwise at the same temperature over one hour, then, after slow cooling, stirring was carried out at 23° C for 15 minutes. The precipitated crystals were filtered and dried to obtain the title compound (629 mg) as a slightly yellow crystal.

Workup

  1. stirringAfter stirring at 40° C for 10 minutes
  2. customseeding, crystals precipitated
  3. stirringAfter stirring at 40° C for 20 minutes
  4. additiontert-butyl methyl ether (10 mL) was added
  5. stirringafter slow cooling, stirring
  6. waitwas carried out at 23° C for 15 minutes
  7. filtrationThe precipitated crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-3f705c6e66ea4fd8a7d8ab5477f53799
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

Loading…