Methanol → HCID 178491901, 화합물

HRID 844190노트

반응식

HRID 844190 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:35])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[NH:19][C:20]([C:22]2[S:23][CH:24]=[C:25]([CH2:28][N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[NH2:34])[C:26]=2[Cl:27])=[O:21])=[N:6][CH:7]=1.S(=O)(=O)(O)O.ClN1[C:46](=[O:47])CCC1=O.[OH2:49].[CH3:50]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:35])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[NH:19][C:20]([C:22]2[S:23][CH:24]=[C:25]([CH2:28][N:29]3[C@H:33]([O:47][CH3:46])[C@H:32]([O:49][CH3:50])[NH:31][C:30]3=[NH:34])[C:26]=2[Cl:27])=[O:21])=[N:6][CH:7]=1

참가 물질

6

반응물 5

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 31398ChlorosuccinimideHCID 167330134-[(2-amino-1H-imidazol-1-yl)methyl]-3-chloro-N-{4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl}thiophene-2-carboxamide

생성물 1

HCID 178491901HCID 178491901, 화합물

실험 절차

To a mixture of N-(5-chloropyridin-2-yl)-2-[((4-((2-aminoimidazol-1-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide (0.053 g, 0.96 mmol) and sulfuric acid (0.10 g, 1.06 mmol) in methanol (10 mL) was added N-chlorosuccinimide (0.192 g, 1.43 mmol). After stirring at ambient temperature for 6 hours, the reaction was poured into water and extracted with ethyl acetate. The ethyl acetate extract was dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography on silica gel to give 0.33 g of N-(5-chloropyridin-2-yl)-2-[((4-((cis-4,5-dimethoxy-2-iminotetrahydroimidazol-1-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide; NMR (CDCl3) 9.0 (d, 2), 8.3 (d, 1), 8.1 (d, 1), 7.7 (dd, 1), 7.5 (s, 1), 7.3 (d, 1), 7.1 (d, 1), 6.0 (br s, 1), 4.8 (m, 2), 4.6 (d, 1), 4.3 (d, 1), 3.9 (s, 3), 3.4 (s, 3), 3.3 (s, 3) ppm.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-90d959d920ee4aa4bfdacfb85b53cb8a
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380221B1

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