Sodium hydride → 6-Amino-7-(4-fluorobenzyl)-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-7,9-dihydro-8H-purin-8-one

HRID 510107노트

반응식

HRID 510107 반응식
[NH2:1][C:2]1[C:7]([N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9](=O)[O:10]C)=[C:6]([NH2:21])[N:5]=[C:4]([N:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[N:23]2)[N:3]=1.[H-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:1][C:2]1[N:3]=[C:4]([N:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])=[N:23]2)[N:5]=[C:6]2[C:7]=1[N:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:9](=[O:10])[NH:21]2

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57330719Methyl {4,6-diamino-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidin-5-yl}(4-fluorobenzyl)carbamate

생성물 1

HCID 569289446-Amino-7-(4-fluorobenzyl)-2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-7,9-dihydro-8H-purin-8-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

21 mg (0.04 mmol) of the compound from example 50A were initially charged in tetrahydrofuran (1.0 ml), 1.8 mg (0.04 mmol) of sodium hydride (60% in mineral oil) were added and the mixture was stirred at 65° C. for 30 min. The reaction mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) and the product fractions were concentrated. This gave 8.5 mg (44% of theory) of the title compound in solid form.

후처리

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was separated by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient)
  6. concentrationthe product fractions were concentrated

출처 및 근거

ORD 기록
ord-62178f1627f846bb9d04ba53f261a0b0
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096592B2

반응 노트

불러오는 중…