4-Toluenesulfonyl chloride → 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

HRID 1027903노트

반응식

HRID 1027903 반응식
[N:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:4](=[O:16])[NH:3][CH:2]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:16][C:4]2[C:5]3[CH2:11][CH2:10][CH2:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[C:6]=3[N:1]=[CH:2][N:3]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1358187063,5,6,7-tetrahydro-4H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-one

생성물 1

HCID 866219036,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

The product from Example 118B (154 mg, 0.72 mmol), p-toluenesulfonyl chloride (278 mg, 1.44 mmol), DMAP (17 mg, 0.14 mmol) in CH2Cl2 (20 mL) was treated with triethylamine (0.25 mL, 1.8 mmol) and stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting with 40% EtOAc/hexanes to provide the title compound. 1H NMR (CDCl3) δ 2.18-2.40 (m, 4H), 2.48 (d, 3H), 2.51-2.58 (m, 2H), 7.25-7.29 (m, 1H), 7.35-7.45 (m, 4H), 7.66-7.73 (m, J=17.63 Hz, 1H), 8.07 (dd, J=15.60, 8.48 Hz, 2H), 8.85 (d, J=8.48 Hz, 1H). MS (M+H)+ m/z 367

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was chromatographed on silica gel eluting with 40% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ed826acc39c14dedbbaf25dae4a106d7
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735411B2

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