N-(4-aminocyclohexyl)methanesulfonamide → HCID 46896669, compound

HRID 1046540Notes

Reaction equation

HRID 1046540 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]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:20][CH2:19]1>CN1C(=O)CCC1.O>[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]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[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 2

HCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 86660234HCID 86660234, compound

Product 1

HCID 46896669HCID 46896669, compoundYield 2.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-(2-chloropyrimidin-4-yl)-imidazo[1,2-a]pyridine (0.125 g), N-(4-amino-cyclohexyl)-methanesulfonamide (0.372 g), and TEA (0.38 mL) in NMP (3 mL) was stirred at 105° C. for 10 h. The reaction mixture was cooled to RT, diluted with water, and the resulting solid filtered, washed with water, and dried. The product was purified by ISCO using 100% DCM to 15% MeOH/DCM, the pure fractions combined and concentrated, then titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide N-[4-(4-imidazo[1,2-a]pyridin-3-yl-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide (compound 10, 5.8 mg).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationthe resulting solid 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-e082c5a5603643e1b754a97343691dff
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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