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Sodium Bicarbonate → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N5-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyrimidine-4,5-diamine

HRID 510064
ノート
印刷プレビュー

反応式

HRID 510064 の反応式
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][N:15]=2)=[N:6]1.[F:26][C:27]([F:37])([F:36])[CH2:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH:21][CH:32]3[CH2:31][CH2:30][N:29]([CH2:28][C:27]([F:37])([F:26])[F:36])[CH2:34][CH2:33]3)=[CH:16][N:15]=2)=[N:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2 回HCID 178400091-(2,2,2-Trifluoroethyl)piperidin-4-one2 回HCID 219348172-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamine

生成物 1

HCID 666348972-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-N5-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyrimidine-4,5-diamine
収率 90.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 887Methanol溶媒

実験手順

200 mg (0.596 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine (synthesis described in US2004/67937; Example V) were initially charged in methanol (16 ml) and admixed with 75 μl (1.312 mmol) of acetic acid, and then 237 mg (1.312 mmol) of 1-(2,2,2-trifluoroethyl)piperidin-4-one were added. After stirring at RT for 15 min, 104 mg (1.67 mmol) of sodium cyanoborohydride were added and the mixture was stirred at RT for 2.5 h. Subsequently, within 2 days, the above-stated amounts of reagents (1-(2,2,2-trifluoroethyl)piperidin-4-one, acetic acid, sodium cyanoborohydride) were added three times, in order to achieve substantially full conversion. Thereafter, saturated aqueous sodium hydrogencarbonate solution (5 ml) was added to the reaction mixture, which was stirred vigorously for 10 min. Subsequently, the reaction mixture was extracted with water and ethyl acetate. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, concentrated and then purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 269 mg of the title compound were obtained (90% of theory).

後処理

  1. stirringthe mixture was stirred at RT for 2.5 h
  2. waitSubsequently, within 2 days
  3. stirringwas stirred vigorously for 10 min
  4. extractionSubsequently, the reaction mixture was extracted with water and ethyl acetate
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

出典と根拠

ORDレコード
ord-2b1fdd82d0c64e3ebd9e76760655ad4a
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096592B2

反応ノート

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