Sodium Bicarbonate → 6-(4-{1-[(8R)-8-(Hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile

HRID 1424095노트

반응식

HRID 1424095 반응식
[Si]([O:8][CH2:9][C@:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][N:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:8][CH2:9][C@:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][N:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 867129436-(4-{1-[(8R)-8-({[t-Butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile

생성물 1

HCID 867129446-(4-{1-[(8R)-8-(Hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinonitrile수율 71.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The compound (375 mg, 0.70 mmol) obtained in Example 61-1) was dissolved in tetrahydrofuran (7 mL). Tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 0.84 mL, 0.84 mmol) was added to the solution at room temperature, and the mixture was stirred at room temperature for 1 h under a nitrogen atmosphere. Saturated aqueous sodium hydrogencarbonate (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 40%) to obtain the title compound (208 mg, 71%) in a white solid form.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 40%)

출처 및 근거

ORD 기록
ord-5fba7edd33ee4cb6ae6edcddf7f9aad4
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927536B2

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