HCID 178461850, compound → HCID 178461849, compound

HRID 869474Notes

Reaction equation

HRID 869474 reaction equation
[SH:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][C@H:12]([C:14]2[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16](=[O:28])[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])[CH3:13])[CH:5]=[CH:4][N:3]=1>CCO>[NH2:8][C:7]1[C:2]([SH:1])=[N:3][CH:4]=[CH:5][C:6]=1[NH:11][C@H:12]([C:14]1[N:15]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:16](=[O:28])[C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][C:18]=2[C:24]([F:25])([F:27])[F:26])[CH3:13]

Participants

3

Reactant 1

HCID 178461850HCID 178461850, compound

Product 1

HCID 178461849HCID 178461849, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-3-(1-(2-mercapto-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoro methyl)isoquinolin-1(2H)-one III-34 (120 mg, 0.247 mmol, 1.0 eq) and stannous chloride dihydrate (297 mg, 1.32 mmol, 5.3 eq) in EtOH (5 mL) was stirred at refluxed for 2 h. The resulting mixture was cooled to RT and concentrated in vacuo. The residue was suspended in water (5 mL), neutralized with saturated NaHCO3 solution to adjust the pH to 7-8 and then extracted with ethyl acetate (5 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product, (S)-3-(1-(3-amino-2-mercaptopyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-35.

Workup

  1. temperatureat refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate (5 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8a3ae5963f5842c68576ad401ce20691
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

Loading…