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Water → HCID 71285599、化合物

HRID 536530
ノート
印刷プレビュー

反応式

HRID 536530 の反応式
[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][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:15]=[C:16](I)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1.C(N(CC)C(C)C)(C)C.Cl.Cl.[NH:42]1[CH2:45][CH:44]([N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:43]1.O>CN1CCCC1=O>[F:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][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:15]=[C:16]([N:42]3[CH2:45][CH:44]([N:46]4[CH2:50][CH2:49][CH2:48][CH2:47]4)[CH2:43]3)[C:17]3[C:22]([CH3:24])([CH3:23])[C:21](=[O:25])[NH:20][C:18]=3[N:19]=2)=[N:6]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 19423677Pyrrolidine, 1-(3-azetidinyl)-, dihydrochlorideHCID 867053672-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

生成物 1

HCID 71285599HCID 71285599、化合物収率 48.3%

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
150 °C

実験手順

150 mg (0.21 mmol, purity approx. 71%) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was dissolved in 1-methyl-2-pyrrolidone (3.1 ml) in a reaction vessel suitable for a microwave, and 0.29 ml (1.66 mmol) of N,N-diisopropyl ethylamine and 165 mg (0.83 mmol) of 1-(azetidin-3-yl)pyrrolidine-dihydrochloride were added. Then the reaction vessel was sealed with a septum and heated in the microwave at 150° C. for 6 h. After cooling, water was added to the reaction mixture. It was stirred for 30 min and filtered to remove the resultant solid. The filtrate was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient). The product fraction was dissolved in dichloromethane and was washed twice with saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated by evaporation. 52 mg of the title compound was obtained (46% of theor.; purity 94%).

後処理

  1. additionwere added
  2. customThen the reaction vessel was sealed with a septum
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. customto remove the resultant solid
  6. customThe filtrate was purified by preparative HPLC (acetonitrile:water (+0.1% trifluoroacetic acid) gradient)
  7. dissolutionThe product fraction was dissolved in dichloromethane
  8. washwas washed twice with saturated aqueous sodium hydrogen carbonate solution
  9. dry with materialThe organic phase was dried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-fe19484c0e6d4d9198975c40a560dce6
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859569B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート