Hydrochloric Acid → 1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine

HRID 1678749Notes

Reaction equation

HRID 1678749 reaction equation
CC(S([NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:24][C:23]3[C:22]4=[N:32][N:33]=[CH:34][N:21]4[CH:20]=[CH:19][C:18]=3[N:17]=2)=[CH:12][CH:11]=1)[CH3:9])=O)(C)C.Cl.O>CO>[C:26]1([C:25]2[C:16]([C:13]3[CH:12]=[CH:11][C:10]([CH:8]([NH2:7])[CH3:9])=[CH:15][CH:14]=3)=[N:17][C:18]3[CH:19]=[CH:20][N:21]4[CH:34]=[N:33][N:32]=[C:22]4[C:23]=3[CH:24]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 594730512-Methyl-N-{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}propane-2-sulfinamide

Product 1

HCID 159792751-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methyl-N-{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}propane-2-sulfinamide (7-3, 180 mg, 0.38 mmol) in methanol (6 mL) was added conc. HCl (1.5 mL). After 1 h, water was added and the mixture was washed with methylene chloride. The aqueous portion was basified with saturated sodium carbonate solution and extracted with methylene chloride. 2N HCl (5 mL) was added to the organic layer and the mixture was concentrated to a minimum volume. The crude product was purified using reverse phase preparative HPLC to give the title compound as a pale yellow solid. LRMS m/z (M+1) Calcd: 366.2. Found 366.3.

Workup

  1. washthe mixture was washed with methylene chloride
  2. extractionextracted with methylene chloride
  3. addition2N HCl (5 mL) was added to the organic layer
  4. concentrationthe mixture was concentrated to a minimum volume
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-15a84619b5334b36855689fd441b7c68
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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