Sodium Bicarbonate → 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid (2-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-6-yl)-amide

HRID 2383273

반응식

HRID 2383273 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][N:8]([CH3:15])[CH2:7][CH2:6][C:5]2=1.[Cl:16][C:17]1[N:18]=[C:19]2[N:23]([C:24]=1[S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:21][S:20]2.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH3:15][N:8]1[CH2:7][CH2:6][C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([NH:1][S:25]([C:24]4[N:23]5[C:19]([S:20][CH:21]=[CH:22]5)=[N:18][C:17]=4[Cl:16])(=[O:26])=[O:27])[CH:3]=3)[NH:11][C:10]=2[CH2:9]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 27997176-Chloroimidazo(2,1-b)(1,3)thiazole-5-sulfonyl chlorideHCID 598434382-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-amine

생성물 1

HCID 156027156-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid (2-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-6-yl)-amide수율 45.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 6-amino-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline (description 2) (150 mg, 0.68 mmol) in pyridine (5 mL) cooled in an ice bath, were added 200 mg of 6-chloro-imidazo[2,1-b]thiazole-5-sulfonyl chloride (0.68 mmol). Under N2, the reaction mixture was left to reach room temperature and stirred for 1 h at this temperature. The reaction mixture was basified with aqueous saturated solution of NaHCO3 and the pyridine evaporated. The mixture was treated with EtOAc and H2O, the organic phase washed with aqueous saturated solution of NaHCO3, separated and dried with Na2SO4. The crude was further purified using SiO2 column chromatography with EtOAc/MeOH/NH3 mixtures to yield 130 mg of 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid (2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-yl)-amide. Cream colored amorphous solid, mp 232-233° C. 1H-NMR (300 MHz, DMSO-d6): (ppm) 2.36 (s, 3H); 2.54 (bb, 2H); 2.61 (bb, 2H); 3.45 (bb, 2H); 6.65 (dd, 1H, J=8.7, 2.1 Hz); 6.99 (d, 1H, J=1.8 Hz); 7.09 (d, 1H, J=8.7 Hz); 7.53 (d, 1H, J=4.5 Hz); 7.81 (d, 1H, J=4.5 Hz); 10.37 (bb, 1H); 10.74 (s, 1H).

후처리

  1. waitUnder N2, the reaction mixture was left
  2. customto reach room temperature
  3. customthe pyridine evaporated
  4. additionThe mixture was treated with EtOAc and H2O
  5. washthe organic phase washed with aqueous saturated solution of NaHCO3
  6. customseparated
  7. dry with materialdried with Na2SO4
  8. customThe crude was further purified

출처 및 근거

ORD 기록
ord-a271cdbbe7f842dab4f96a943b03a1cc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263609B2

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