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

HRID 550430노트

반응식

HRID 550430 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6baaeeb0bb2d4adeaea09b48fd57b903
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947676B2

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