Water → HCID 46896670, compound

HRID 1046541Notes

Reaction equation

HRID 1046541 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:17][CH:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1.O>CN1C(=O)CCC1>[N:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:17][CH:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]3)[N:7]=2)[N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=12

Participants

5

Reactant 3

HCID 962WaterHCID 812934-AminocyclohexanolHCID 86660234HCID 86660234, compound

Product 1

HCID 46896670HCID 46896670, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-(2-chloropyrimidin-4-yl)-imidazo[1,2-a]pyridine (30 mg) and 4-amino-cyclohexanol (45 mg) in NMP (1 mL) was stirred at 105° C. for 5 h. The reaction mixture was then cooled to RT and titurated with water. The resulting solid was filtered, washed with water and dried. The product was purified by ISCO using 100% DCM to 15% MeOH/DCM, and the pure fractions combined, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide 4-(4-imidazo[1,2-a]pyridin-3-yl-pyrimidin-2-ylamino)-cyclohexanol (compound 11, 22 mg).

Workup

  1. temperatureThe reaction mixture was then cooled to RT
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customdried
  5. customThe product was purified by ISCO
  6. concentrationconcentrated
  7. filtrationThe resulting solid was filtered
  8. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-6a12cdc7d19847beb7387ad5073ec7a1
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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