4-Toluenesulfonyl chloride → HCID 178481314、化合物

HRID 73268

反応式

HRID 73268 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 178481314HCID 178481314、化合物収率 17.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c9ec690374044a349d0f72f36e8325ba
出典データセット
uspto-grants-2014_09
特許番号
US08829036B2

関連ノート

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