Triethylamine → tert-Butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-{[(3-ethoxy-3-oxopropyl)-sulfonyl]amino}-1H-indazole-1-carboxylate

HRID 1038389

반응식

HRID 1038389 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[C:16]([C:17]#[N:18])=[C:15]([CH3:19])[NH:14][C:13]([CH3:20])=[C:12]3[C:21]#[N:22])[CH:9]=2)[N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:3]=1.Cl[S:31]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=[O:33])=[O:32].C(N(CC)CC)C>ClCCl>[C:21]([C:12]1[CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:3]=[C:2]3[NH:1][S:31]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=[O:33])=[O:32])[C:16]([C:17]#[N:18])=[C:15]([CH3:19])[NH:14][C:13]=1[CH3:20])#[N:22]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 4128467Ethyl 3-(chlorosulfonyl)propanoateHCID 24959832tert-Butyl 3-amino-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazole-1-carboxylate

생성물 1

HCID 67354474tert-Butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-{[(3-ethoxy-3-oxopropyl)-sulfonyl]amino}-1H-indazole-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 200 mg (0.512 mmol) tert-butyl 3-amino-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazole-1-carboxylate (Example 3A) in dichloromethane (4 ml) were added 309 mg (1.54 mmol) ethyl 3-(chlorosulfonyl)propanoate and 0.21 ml (1.54 mmol) triethylamine. The mixture was stirred at room temperature for 12 h and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with saturated aqueous sodium hydrogencarbonate solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 41 mg (14% of th.) of the title compound.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative RP-HPLC (acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-2a08aa8f6aa34e08b37ca9af4886d18e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551989B2

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