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

HRID 1484451

반응식

HRID 1484451 반응식
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]

참가 물질

4

반응물 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

생성물 1

HCID 178485216HCID 178485216, 화합물수율 69%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-efd19343a54c46ca985cd9c28e61078d
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422244B2

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