18-Crown-6 → HCID 117667385、化合物

HRID 1526236ノート

反応式

HRID 1526236 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][OH:46])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.O.O1CCOCC1>[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][O:46][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

8

反応物 4

HCID 2855718-Crown-6HCID 719766(R)-1-N-Benzyl-prolinolHCID 23665647Potassium tert-butoxideHCID 885697085-Chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide

生成物 1

HCID 117667385HCID 117667385、化合物収率 50.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (300 mg), [(2R)-1-benzylpyrrolidin-2-yl]methanol (251 mg), 18-crown-6 (346 mg), potassium t-butoxide (147 mg), and dioxane (3 mL) was stirred at 100° C. for 5 hours. To the mixture were added water and ethyl acetate, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1) to obtain 5-{[(2R)-1-benzylpyrrolidin-2-yl]methoxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (201 mg) as a yellow solid.

後処理

  1. customfollowed by liquid separation
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1)

出典と根拠

ORDレコード
ord-7737effb7d70488181e35ce49d2d0d5d
出典データセット
uspto-grants-2015_07
特許番号
US09085540B2

反応ノート

読み込み中…