Methanesulfonyl chloride → 2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate

HRID 550430ノート

反応式

HRID 550430 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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][OH:30])[C:19]=23)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[CH3:31][S:32]([O:30][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:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:24][N:25]=1)(=[O:34])=[O:33]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 115966542-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanol

生成物 1

HCID 115114392-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate収率 78%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanol (prepared as described in Example 7/500 mg, 1.22 mmol) was dissolved in dry pyridine (12 ml) and methanesulfonyl chloride (142 μl, 1.84 mmol) was added drop-wise under argon. The mixture was stirred for 1 hour at room temperature then partitioned between water and methylene chloride. The organic layer was washed with water, dried over MgSO4 and evaporated under vacuum. The residue was triturated in ether, filtered and dried to give the title compound as a tan solid (462 mg, 78%); NMR Spectrum: 3.28 (s, 3H), 3.80 (s, 3H), 4.58 (d, 2H), 4.69 (d, 2H), 5.16 (s, 2H), 7.03 (d, 2H), 7.37 (m, 3H), 7.55 (d, 1H), 7.85 (td, 1H), 8.13 (s, 1H), 8.29 (s, 1H), 8.58 (d, 1H).

後処理

  1. customthen partitioned between water and methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue was triturated in ether
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-6baaeeb0bb2d4adeaea09b48fd57b903
出典データセット
uspto-grants-2011_05
特許番号
US07947676B2

反応ノート

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