4-Toluenesulfonyl chloride → HCID 178481314, 화합물

HRID 1927163노트

반응식

HRID 1927163 반응식
C(OC([C@H:8]1[NH:13][C:12]([CH3:18])([C:14]([NH:16][NH2:17])=[O:15])[CH2:11][C:10](=[O:19])[N:9]1[CH3:20])=O)(C)(C)C.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=O)[CH:25]=[CH:26][CH:27]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.CC[N:44](CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]2[O:15][C:14]([C@@:12]3([CH3:18])[NH:13][C:8](=[NH:44])[N:9]([CH3:20])[C:10](=[O:19])[CH2:11]3)=[N:16][N:17]=2)[CH:25]=[CH:26][CH:27]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 67303828(S)-2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carbohydrazide

생성물 1

HCID 178481314HCID 178481314, 화합물수율 17.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

실험 절차

To a solution of (S)-2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carbohydrazide (CY1, R6=Me, 0.030 g, 0.10 mmol) in DCM (0.25 mL) was added 3-chlorophenylisocyanate (0.015 mL, 0.20 mmol, 2 eq). The mixture was stirred at RT for 3 h and volatiles were then removed in vacuo. The residue was treated with TsCl (0.020 g, 0.10 mmol, 1 eq), Et3N (0.083 mL, 0.60 mmol, 6 eq), and DMAP (0.002 g, 0.016 mmol, 0.16 eq) in DCM (0.25 mL) at RT for 16 h. The mixture was diluted with DCM (20 mL), washed with H2O (10 mL) and saturated brine (10 mL), and concentrated in vacuo. The residue was treated with 30% TFA/DCM (1 mL) at RT for 1 h. The mixture was concentrated in vacuo and the residue was purified on reverse phase HPLC (B) to give 0.006 g (10%) of (S)-6-(5-(3-chlorophenylamino)-1,3,4-oxadiazol-2-yl)-2-imino-3,6-dimethyl-tetrahydropyrimidin-4(1H)-one (DA1; R6=Me). 1HNMR (CD3OD, 300 MHz): 7.78 (t, 1H), 7.47 (m, 2H), 7.17 (dt, 1H), 3.53 (m, 2H), 3.36 (s, 3H), 1.78 (s, 3H). MS (ESI): MH+=335.3, HPLC (A) Rt=5.710 min.

후처리

  1. customvolatiles were then removed in vacuo
  2. washwashed with H2O (10 mL) and saturated brine (10 mL)
  3. concentrationconcentrated in vacuo
  4. additionThe residue was treated with 30% TFA/DCM (1 mL) at RT for 1 h
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe residue was purified on reverse phase HPLC (B)

출처 및 근거

ORD 기록
ord-2ab2c895bf364e3bba08dc6baf7d392c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183252B2

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