1,2-Dichloroethane → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(5-(N-(4-(dimethylcarbamoyl)phenyl)-sulfamoyl)thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide

HRID 59760노트

반응식

HRID 59760 반응식
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].C(Cl)CCl.[Cl:28][C:29]1[CH:30]=[N+:31]([O-:54])[CH:32]=[C:33]([Cl:53])[C:34]=1[CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([F:47])[F:46])=[C:40]([O:48][CH2:49][CH:50]2[CH2:52][CH2:51]2)[CH:39]=1)O>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Cl:28][C:29]1[CH:30]=[N+:31]([O-:54])[CH:32]=[C:33]([Cl:53])[C:34]=1[CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH:45]([F:47])[F:46])=[C:40]([O:48][CH2:49][CH:50]2[CH2:52][CH2:51]2)[CH:39]=1)[O:21][C:20]([C:18]1[S:19][C:15]([S:12](=[O:14])(=[O:13])[NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:3](=[O:4])[N:2]([CH3:23])[CH3:1])=[CH:6][CH:7]=2)=[CH:16][CH:17]=1)=[O:22]

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-oxideHCID 867038655-(N-(4-(dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylic acid

생성물 1

HCID 72706890(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(5-(N-(4-(dimethylcarbamoyl)phenyl)-sulfamoyl)thiophene-2-carbonyloxy)ethyl)pyridine 1-oxide수율 13%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

5-(N-(4-(dimethylcarbamoyl)phenyl)sulfamoyl)thiophene-2-carboxylic acid (Int. 76) (54 mg, 0.152 mmol), DMAP (6.20 mg, 0.051 mmol), and EDC (38.9 mg, 0.203 mmol) were dissolved in DMF. (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (42.7 mg, 0.102 mmol) was added. The reaction was stirred at RT for 4 hours. The reaction mixture was diluted with water and extracted with AcOEt. The organic phase was dried over Na2SO4 and concentrated under vacuum to give a crude product which was purified by preparative HPLC-Method 2 to give 10 mg of the desired product (Compound 77).

후처리

  1. extractionextracted with AcOEt
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customto give a crude product which
  5. customwas purified by preparative HPLC-Method 2

출처 및 근거

ORD 기록
ord-d1bb2cf791904e1cbb8bcf0039712f40
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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