Methanol → HCID 178491901、化合物

HRID 2300950ノート

反応式

HRID 2300950 の反応式
[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

参加物

6

反応物 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

生成物 1

HCID 178491901HCID 178491901、化合物

実験手順

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-((cis4,5-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.

後処理

  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

出典と根拠

ORDレコード
ord-555a7f2c4d6041148da8809c1aef43bf
出典データセット
uspto-grants-2002_12
特許番号
US06498185B1

反応ノート

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