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

HRID 587140

반응식

HRID 587140 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-99e9f0a35c3240d5a54ba40f06690f37
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226929B2

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