Ethyl 4-aminocyclohexanecarboxylate → HCID 67426454, compound

HRID 1516433Notes

Reaction equation

HRID 1516433 reaction equation
[I:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1)=[O:24])[CH3:21]>O1CCOCC1.CCO>[CH2:20]([O:22][C:23]([CH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:13]2[N:12]=[C:11]([N:7]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([I:1])[C:10]=4[N:9]=[N:8]3)[CH:16]=[CH:15][N:14]=2)[CH2:27][CH2:26]1)=[O:24])[CH3:21]

Participants

5

Reactant 2

HCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 68604454HCID 68604454, compound

Product 1

HCID 67426454HCID 67426454, compoundYield 139.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-iodo-1-(2-methylsulfinyl-pyrimidin-4-yl)-1H-benzotriazole (2.0 g) and 4-amino-cyclohexanecarboxylic acid ethyl ester (1.8 g) in 1,4-dioxane (25 mL) was stirred at 110° C. for 4 h. The solvent was removed in vacuo to provide an oil, which was taken up in EtOH and heated in a water bath until a light orange solid formed. The solid was filtered, washed with Et2O, and dried to provide 4-[4-(4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexane-carboxylic acid ethyl ester (3.56 g, 93%) as a light orange powder.

Workup

  1. customThe solvent was removed in vacuo
  2. customto provide an oil, which
  3. temperatureheated in a water bath until a light orange solid
  4. customformed
  5. filtrationThe solid was filtered
  6. washwashed with Et2O
  7. customdried

Sources & evidence

ORD record
ord-63c0510bc1eb48a18db8d99ade8acdb3
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

Loading…