Ethyl 4-aminocyclohexanecarboxylate → HCID 59743409, compound

HRID 1947058Notes

Reaction equation

HRID 1947058 reaction equation
C(S([C:8]1[N:13]=[C:12]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([C:23]([NH2:25])=[O:24])=[CH:15]2)[CH:11]=[CH:10][N:9]=1)(=O)=O)CCC.[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]1)=[O:30])[CH3:27]>O1CCOCC1>[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:8]2[N:13]=[C:12]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]([C:23](=[O:24])[NH2:25])=[CH:15]3)[CH:11]=[CH:10][N:9]=2)[CH2:33][CH2:32]1)=[O:30])[CH3:27]

Participants

4

Reactant 2

HCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 69311939HCID 69311939, compound

Product 1

HCID 59743409HCID 59743409, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(2-Butylsulfonyl-pyrimidin-4-yl)-1H-indole-3-carboxylic acid amide (1.5568 g, 4.349 mmol) was dissolved in dry dioxane (150 mL), and 4-amino-cyclohexanecarboxylic acid ethyl ester (1.86 g, 10.87 mmol) was added. The mixture was heated at reflux overnight, then evaporated to dryness, poured into water, extracted into EtOAc, and dried under vacuum. The product was recrystallized from EtOH-free CHCl3 to provide 4-[4-(3-carbamoyl-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (1.477 g, 83% yield) as a white solid (Compound 322).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customevaporated to dryness
  4. additionpoured into water
  5. extractionextracted into EtOAc
  6. customdried under vacuum
  7. customThe product was recrystallized from EtOH-free CHCl3

Sources & evidence

ORD record
ord-878975b03ee24eb4a34f8c254f0b20ae
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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