Methanol → HCID 59612443, compound

HRID 472581Notes

Reaction equation

HRID 472581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][C:19]3[CH:33]=[CH:32][C:22]4[CH2:23][CH2:24][N:25]([CH2:28][CH2:29]SC)[CH2:26][CH2:27][C:21]=4[CH:20]=3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1.O[O:35][S:36]([O-:38])=O.[K+].[CH3:40]O>O>[CH3:40][S:36]([CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][C:22]2[CH:32]=[CH:33][C:19]([NH:18][C:16]3[N:17]=[C:10]4[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])=[CH:14][CH:13]=[CH:12][N:11]4[N:15]=3)=[CH:20][C:21]=2[CH2:27][CH2:26]1)(=[O:38])=[O:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 67481488HCID 67481488, compound

Product 1

HCID 59612443HCID 59612443, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To [8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-[3-(2-methylsulfanyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-amine (0.173 g, 0.376 mmol) in methanol (5 mL) was added oxone (0.694 g, 1.13 mmol) in water (2.5 mL) and was stirred at room temperature for 2 hours and concentrated. The reaction was partitioned between dichloromethane/1N sodium carbonate, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using Prep TLC plates (5% methanol in dichloromethane) and concentrated to give [3-(2-methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-[8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-amine (0.025 g, 14%). MP=91-94° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.75 (d, 1H), 7.55 (m, 2H), 7.40 (m, 2H), 7.32 (s, 1H), 7.18 (d, 1H), 7.05 (m, 3H), 3.75 (s, 3H), 3.28 (m, 2H), 3.18 (s, 3H), 2.85 (m, 2H), 2.75 (m, 4H), 2.58 (m, 4H): MS=492 (MH)+.

Workup

  1. concentrationconcentrated
  2. customThe reaction was partitioned between dichloromethane/1N sodium carbonate
  3. washwashed with water/brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-425291ab635548839f9619e9f6eaaa6c
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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