1,1'-Carbonyldiimidazole → 2-[[(2S)-1-[(4-Methoxy-2,6-dimethyl-phenyl)sulfonyl]-1,2,3,4-tetrahydro-quinolin-2-yl]-methoxy]-1-(3-pyridin-4-yl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridin-5-yl)-ethanone

HRID 2388690Notes

Reaction equation

HRID 2388690 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26](O)=[O:27])(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:42]1[CH:47]=[CH:46][C:45]([C:48]2[C:52]3[CH2:53][NH:54][CH2:55][CH2:56][C:51]=3[O:50][N:49]=2)=[CH:44][CH:43]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:29])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26]([N:54]2[CH2:55][CH2:56][C:51]3[O:50][N:49]=[C:48]([C:45]4[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=4)[C:52]=3[CH2:53]2)=[O:27])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 46222615(S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic AcidHCID 579486603-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

Product 1

HCID 579486592-[[(2S)-1-[(4-Methoxy-2,6-dimethyl-phenyl)sulfonyl]-1,2,3,4-tetrahydro-quinolin-2-yl]-methoxy]-1-(3-pyridin-4-yl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridin-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic acid (AC31) (0.13 g, 0.31 mmol) was dissolved in dichloromethane (4 ml) and 1,1′-carbonyldiimidazole (53 mg, 0.325 mmol) was added. After the mixture had been stirred at room temperature for 1 h, 3-(pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine (AM5) (62 mg, 0.31 mmol) in dichloromethane (4 ml) was added and the mixture was stirred at room temperature overnight. Saturated sodium hydrogen carbonate solution was added to the reaction mixture, the aqueous phase was extracted with dichloromethane (2×) and the combined organic phases were washed with saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica) with ethyl acetate/hexane 20/1. Yield: 0.13 g (77%). MS, Rt=4.8 min, m/z=603.1 [MH]+

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe aqueous phase was extracted with dichloromethane (2×)
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica) with ethyl acetate/hexane 20/1

Sources & evidence

ORD record
ord-0ffca944c2984eea8066d935e5e9a369
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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