Potassium Carbonate → 3-[(4-(4,4-Difluoropiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

HRID 587140

反応式

HRID 587140 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.[F:27][C:28]1([F:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>CS(C)=O.CCOC(C)=O>[F:27][C:28]1([F:34])[CH2:33][CH2:32][N:31]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=3)[N:3]=2)[CH2:30][CH2:29]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

生成物 1

HCID 601971023-[(4-(4,4-Difluoropiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of triazine A1 (270 mg, 0.9 mmol) in DMSO (0.9 mL) were added K2CO3 (370 mg, 2.7 mmol) and 4,4-difluoropiperidine hydrochloride (140 mg, 0.9 mmol). The mixture was stirred for 2 hours at 80° C. After cooling to room temperature it was diluted with EtOAc and extracted with water. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was stirred with DCM to give the solid title compound B2 which was isolated by filtration and dried in vacuo (white powder, 110 mg, 32%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 1.90-2.15 (m, 4H), 3.81-3.98 (m, 4H), 4.21 (s, 2H), 6.88 (s, 2H), 6.98-7.04 (m, 1H), 7.21-7.34 (m, 1H), 7.44-7.60 (m, 1H), 7.78-7.90 (m, 1H), 8.25 (s, 1H), 9.77 (s, 1H). MS (ES) C15H18F2N6O2S requires: 384. found: 385 (M+H)+.

後処理

  1. temperatureAfter cooling to room temperature it
  2. extractionextracted with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. stirringThe residue was stirred with DCM

出典と根拠

ORDレコード
ord-99e9f0a35c3240d5a54ba40f06690f37
出典データセット
uspto-grants-2016_01
特許番号
US09226929B2

関連ノート

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