Triethylamine → (5-(4-Methoxy-2,6-dimethylphenylsulfonyl)-4,5,6,7-tetrahydrothieno-[3,2-c]pyridin-2-yl)(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)methanone

HRID 1808370Notes

Reaction equation

HRID 1808370 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:16][CH2:15][N:14]([C:17]([C:19]4[S:27][C:26]5[CH2:25][CH2:24][NH:23][CH2:22][C:21]=5[CH:20]=4)=[O:18])[CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:37][O:38][C:39]1[CH:44]=[C:43]([CH3:45])[C:42]([S:46](Cl)(=[O:48])=[O:47])=[C:41]([CH3:50])[CH:40]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH3:50])[C:42]([S:46]([N:23]2[CH2:24][CH2:25][C:26]3[S:27][C:19]([C:17]([N:14]4[CH2:15][CH2:16][C:11]5([CH2:28][CH2:29][N:8]([C:5]6[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=6)[CH2:9][CH2:10]5)[CH2:12][CH2:13]4)=[O:18])=[CH:20][C:21]=3[CH2:22]2)(=[O:47])=[O:48])=[C:43]([CH3:45])[CH:44]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 68507109(9-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)methanone hydrochloride

Product 1

HCID 46897099(5-(4-Methoxy-2,6-dimethylphenylsulfonyl)-4,5,6,7-tetrahydrothieno-[3,2-c]pyridin-2-yl)(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(9-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)(4,5,6,7-tetrahydrothieno[3,2-c]-pyridin-2-yl)methanone hydrochloride (89 mg, 0.208 mmol) was dissolved in dichloromethane (5 ml) and cooled, and triethylamine (0.07 ml, 0.52 mmol) was added thereto. At 0° C., a solution of 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (50 mg, 0.208 mmol) in dichloromethane (5 ml) was added dropwise, and then stirring was carried out for 15 h at room temperature. Saturated sodium hydrogen carbonate solution (10 ml) was added, the mixture was stirred for 15 min. and the phases were separated. The aqueous phase was extracted with dichloromethane (30 ml), and then the combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/-ammonia (25% aq.), 400:20:1). Yield: 70 mg (56%). MS, R=3.4 min; m/z=595.3 [MH]+

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for 15 min.
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with dichloromethane (30 ml)
  5. washthe combined organic phases were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/-ammonia (25% aq.), 400:20:1)
  9. customMS, R=3.4 min

Sources & evidence

ORD record
ord-7da7df7e0e6f496bb91f645c90492d90
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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