Methanol → HCID 117770048, compound

HRID 1526369Notes

Reaction equation

HRID 1526369 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:35])[N:8]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])[CH:9]=[C:10]([C:11]3[CH:16]=[N:15][C:14]([O:17]CC4C=CC(OC)=CC=4)=[CH:13][N:12]=3)[C:5]=2[NH:4][N:3]=1.CO.O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[NH2:1][C:2]1[C:6]2[C:7](=[O:35])[N:8]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])[CH:9]=[C:10]([C:11]3[N:12]=[CH:13][C:14](=[O:17])[NH:15][CH:16]=3)[C:5]=2[NH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 117770748HCID 117770748, compound

Product 1

HCID 117770048HCID 117770048, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 3-amino-5-(2,6-difluorophenyl)-7-(5-((4-methoxybenzyl)oxy)pyrazin-2-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Example 151 (133 mg) were added methanol (2 mL), tetrahydrofuran (3 mL) and p-toluenesulfonic acid monohydrate (53 mg), and the reaction mixture was stirred at room temperature for 1 hr. p-Toluenesulfonic acid monohydrate (53 mg) was added thereto, and the reaction mixture was stirred at room temperature for 5 hr. To the reaction mixture were added triethylamine (97 μL) and silica gel, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/methanol). The obtained residue was crystallized from ethyl acetate/diethyl ether to give the title compound (92 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 5 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (ethyl acetate/methanol)
  4. customThe obtained residue was crystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-b0f20d2067f149e4bfb380a3866f3baa
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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