Sodium Bicarbonate → HCID 136336864, 화합물

HRID 69135

반응식

HRID 69135 반응식
[CH3:1][C:2]1[C:3]([C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.[N:30]1([C:35]2[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][N:36]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCCl>[CH3:1][C:2]1[C:3]([C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH2:39][C:38]3[CH:37]=[N:36][C:35]([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:42][CH:41]=3)[CH2:26][CH2:25]2)=[O:23])=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 27947756-(Pyrrolidin-1-yl)pyridine-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136336865HCID 136336865, 화합물

생성물 1

HCID 136336864HCID 136336864, 화합물수율 58%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매

실험 절차

To a mixture of 11.9 mg of 7-methyl-8-(piperazin-1-ylcarbonyl)-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one, 15.9 mg of 6-(1-pyrrolidinyl)nicotinaldehyde, 0.3 mL of 1,2-dichloroethane, and 30 μL of acetic acid was added 19.1 mg of sodium triacetoxyborohydride, followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution) to obtain 9.7 mg of 7-methyl-8-[(4-{[6-(pyrrolidin-1-yl)pyridin-3-yl]methyl}piperazin-1-yl)carbonyl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one.

후처리

  1. extractionfollowed by extraction with chloroform
  2. customThe organic layer was evaporated under reduced pressure
  3. customThe obtained residue was purified by preparative HPLC (methanol/0.1% aqueous formic acid solution)

출처 및 근거

ORD 기록
ord-d740bd3976804cf9a987ed6f755e162f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822448B2

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