Dimethylformamide → 3-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550428ノート

反応式

HRID 550428 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[CH:22][N:21]=[C:20]3[NH:24][N:25]=[C:26]([O:27][CH2:28][CH2:29]O)[C:19]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.CN(C=O)C.S(Cl)([Cl:38])=O>>[Cl:38][CH2:29][CH2:28][O:27][C:26]1[C:19]2[C:20](=[N:21][CH:22]=[N:23][C:18]=2[NH:17][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)=[C:2]([Cl:1])[CH:3]=2)[NH:24][N:25]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 116405472-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethanol

生成物 1

HCID 117050313-(2-chloroethoxy)-N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

実験手順

2-{[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethanol (prepared as described in Example 1/550 mg, 1.28 mmol) was dissolved in thionyl chloride (4 ml). DMF (20 μl) was added and the mixture refluxed for 2 hours under a dry atmosphere. After evaporation of the solvent under reduced pressure, the solid residue was triturated in ether, filtered and dried under vacuum to provide the title compound as a hydrochloride salt (551 mg, 89%); NMR Spectrum: 4.03 (t, 2H), 4.58 (t, 2H), 5.28 (s, 2H), 7.18 (t, 1H), 7.29-7.34 (m, 3H), 7.45-7.53 (m, 2H), 7.83 (s, 1H), 8.32 (s, 1H), 9.25 (br s, 1H).

後処理

  1. temperaturethe mixture refluxed for 2 hours under a dry atmosphere
  2. customAfter evaporation of the solvent under reduced pressure
  3. customthe solid residue was triturated in ether
  4. filtrationfiltered
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-a1e83e94863d485092d68b2ec21ac5ea
出典データセット
uspto-grants-2011_05
特許番号
US07947676B2

反応ノート

読み込み中…