Ethyl 4-aminocyclohexanecarboxylate → HCID 46896668, compound

HRID 1046534Notes

Reaction equation

HRID 1046534 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)=[CH:16][N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1)=[O:29])[CH3:26]>CN1C(=O)CCC1.O>[CH2:25]([O:27][C:28]([CH:30]1[CH2:35][CH2:34][CH:33]([NH:36][C:20]2[N:19]=[C:18]([C:15]3[N:11]4[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[C:10]4=[N:17][CH:16]=3)[CH:23]=[CH:22][N:21]=2)[CH2:32][CH2:31]1)=[O:29])[CH3:26]

Participants

5

Reactant 2

HCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 86660233HCID 86660233, compound

Product 1

HCID 46896668HCID 46896668, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-benzyloxy-3-(2-chloropyrimidin-4-yl)-imidazo[1,2-a]pyridine (0.19 g) and 4-amino-cyclohexanecarboxylic acid ethyl ester (0.29 g) in NMP (1 mL) was stirred at 100° C. for 1 h. The reaction mixture was cooled to RT, diluted with water, and the resulting solid separated, washed with water, and dried. The solid was titurated with hot EtOAc and filtered to provide 4-[4-(8-benzyloxy-imidazo[1,2-a]pyridine-3-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (compound 8, 0.25 g), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe resulting solid separated
  3. washwashed with water
  4. customdried
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7bb629898b90436dbd2a84ebbaf14c30
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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