Pyridine → N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)-5-methyl-2-(trifluoromethyl)furan-3-sulfonamide

HRID 1505535ノート

反応式

HRID 1505535 の反応式
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:16]([C:17]2[N:25]=[CH:24][N:23]=[C:22]3[C:18]=2[N:19]=[CH:20][N:21]3[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:15][CH:14]=[CH:13][N:12]=1.[CH3:32][C:33]1[O:37][C:36]([C:38]([F:41])([F:40])[F:39])=[C:35]([S:42](Cl)(=[O:44])=[O:43])[CH:34]=1.N1C=CC=CC=1>ClCCl>[F:1][C:2]1[C:3]([NH:10][C:11]2[C:16]([C:17]3[N:25]=[CH:24][N:23]=[C:22]4[C:18]=3[N:19]=[CH:20][N:21]4[CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[NH:8][S:42]([C:35]1[CH:34]=[C:33]([CH3:32])[O:37][C:36]=1[C:38]([F:41])([F:39])[F:40])(=[O:44])=[O:43]

参加物

5

反応物 3

HCID 1049PyridineHCID 27798955-methyl-2-(trifluoromethyl)furan-3-sulfonyl ChlorideHCID 867029472,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine

生成物 1

HCID 86702972N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)-5-methyl-2-(trifluoromethyl)furan-3-sulfonamide収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

The 2,6-difluoro-N1-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)benzene-1,3-diamine (50 mg, 0.120 mmol) prepared at Step 9 was added and dissolved into dichloromethane solvent. 5-methyl-2-(trifluoromethyl)furan-3-sulfonyl chloride (24 mg, 0.130 mmol) and pyridine (11 uL, 0.130 mmol) were added into the reaction solution and stirred at 50° C. for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 72 mg of the target compound, N-(2,4-difluoro-3-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)phenyl)-5-methyl-2-(trifluoromethyl)furan-3-sulfonamide (percentage yield: 94%), was obtained.

後処理

  1. additionwas added
  2. customAfter the reaction
  3. washthe reactant was washed with 1N aqueous hydrochloric acid solution and salt water
  4. extractionAfter extraction with dichloromethane
  5. dry with materialthe organic layer was dried with sulfuric anhydride magnesium and vacuum
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-43c640147abf42c1a21b0c14992f3c0f
出典データセット
uspto-grants-2015_12
特許番号
US09216981B2

反応ノート

読み込み中…