6-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamide → HCID 178485216、化合物

HRID 1484451ノート

反応式

HRID 1484451 の反応式
CS[C:3]([N:6]1[N:10]=[CH:9][C:8]2([CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:7]1)=[N:4][CH3:5].[Cl:16][C:17]1[N:18]=[C:19]2[N:23]([C:24]=1[S:25]([NH2:28])(=[O:27])=[O:26])[CH:22]=[CH:21][S:20]2>C(#N)C>[CH3:5][NH:4][C:3]([N:6]1[N:10]=[CH:9][C:8]2([CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH2:7]1)=[N:28][S:25]([C:24]1[N:23]2[C:19]([S:20][CH:21]=[CH:22]2)=[N:18][C:17]=1[Cl:16])(=[O:27])=[O:26]

参加物

4

反応物 2

HCID 27798396-Chloroimidazo[2,1-b][1,3]thiazole-5-sulfonamideHCID 67360788N-methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester

生成物 1

HCID 178485216HCID 178485216、化合物収率 69%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

0.42 g (1 mol equiv.) N-Methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester and 0.46 g (1.05 mol equiv.) 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid amide were added to 7 mL acetonitrile and the reaction mixture was refluxed overnight. Volatiles were removed under reduced pressure, and the residue was taken up in ethylacetate and extracted with 2N NaOH. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Purification by flash chromatography on silica gel (EtOAc) afforded 0.56 g (69%) 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid methylamino-(8-oxa-2,3-diaza-spiro[4.5]dec-3-en-2-yl)-methylene-amide. 1H NMR (400 MHz, CDCl3) δ 1.51-1.57 (m, 2H), 1.80-1.89 (m, 2H), 3.10 (d, J=5.0 Hz, 3H), 3.51-3.59 (m, 2H), 3.83-3.90 (m, 4H), 3.89 (s, 2H), 6.89 (s, 1H), 6.99 (d, J=4.6 Hz, 1H), 7.12 (br.s., 1H), 8.01 (d, J=4.6 Hz, 1H).

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. customVolatiles were removed under reduced pressure
  3. extractionextracted with 2N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography on silica gel (EtOAc)

出典と根拠

ORDレコード
ord-efd19343a54c46ca985cd9c28e61078d
出典データセット
uspto-grants-2016_08
特許番号
US09422244B2

反応ノート

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