Water → 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester

HRID 237429ノート

反応式

HRID 237429 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[C:12]([O:17][CH2:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH:5]=[CH:4][N:3]=1.Cl.[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]1)=[O:30])C.C([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1>[CH3:26][O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:2]2[N:7]=[C:6]([N:8]3[C:16]4[C:11](=[C:12]([O:17][CH2:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=[CH:14][CH:15]=4)[CH:10]=[CH:9]3)[CH:5]=[CH:4][N:3]=2)[CH2:33][CH2:32]1)=[O:30]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11586508trans-Ethyl 4-aminocyclohexanecarboxylate hydrochlorideHCID 580170801-(2-chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole

生成物 1

HCID 580170934-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester収率 97%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

1-(2-Chloro-pyrimidin-4-yl)-4-(3-methanesulfonyl-propoxy)-1H-indole (300 g), 4-amino-cyclohexanecarboxylic acid ethyl ester HCl salt (155 g), and K2CO3(170 g) in NMP (2.35 L) were stirred at 80° C. for 5 h and then stirred overnight at room temperature. The reaction mixture was then stirred on an ice bath, and 2.5 L water was slowly added while stirring, and cooling continued until completion of the exothermic reaction. Upon cooling, the mixture was filtered, and resulting solid was rinsed with H2O and dried in vacuo overnight to yield 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (97%).

後処理

  1. stirringThe reaction mixture was then stirred on an ice bath
  2. stirringwhile stirring
  3. temperaturecooling
  4. customcontinued until completion of the exothermic reaction
  5. temperatureUpon cooling
  6. filtrationthe mixture was filtered
  7. customresulting solid
  8. washwas rinsed with H2O
  9. customdried in vacuo overnight

出典と根拠

ORDレコード
ord-71369965bd674f87bb96abca0888c387
出典データセット
uspto-grants-2014_02
特許番号
US08642601B2

反応ノート

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