1,2-Dichloroethane → HCID 86681601, 화합물

HRID 571178노트

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HRID 571178 반응식
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[C:28]([O:32][C:33]([NH:35][C:36]1[CH:44]=[C:43]2[C:39]([CH2:40][N:41]([CH2:46][C:47](O)=[O:48])[C:42]2=[O:45])=[CH:38][CH:37]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[C:28]([O:32][C:33]([NH:35][C:36]1[CH:44]=[C:43]2[C:39]([CH2:40][N:41]([CH2:46][C:47]([O:10][C@H:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]4[CH2:25][CH2:24]4)[CH:12]=3)[CH2:8][C:7]3[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=3[Cl:1])=[O:48])[C:42]2=[O:45])=[CH:38][CH:37]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide2회HCID 86681600HCID 86681600, 화합물

생성물 1

HCID 86681601HCID 86681601, 화합물수율 69.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (Compound 7, 60 mg, 0.143 mmol), 2-(6-(tert-butoxycarbonylamino)-1-oxoisoindolin-2-yl)acetic acid (65.6 mg, 0.214 mmol), DMAP (20.93 mg, 0.171 mmol), and EDC (82 mg, 0.428 mmol) were dissolved in DMF (5 ml). The reaction was stirred at RT overnight. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in EtOAc and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give (S)-4-(2-(2-(6-(tert-butoxycarbonylamino)-1-oxoisoindolin-2-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (70 mg, 0.099 mmol, 69% yield). MS/ESI+ 306.12 [MH]+

후처리

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in EtOAc
  3. extractionextracted with HCl 1N, Na2CO3 sat. sol. and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-ff1fdee909ff4c5b9c9f10a4465d3e15
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

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