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

反応式

HRID 1038389 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2a08aa8f6aa34e08b37ca9af4886d18e
出典データセット
uspto-grants-2013_10
特許番号
US08551989B2

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