N-(4-aminocyclohexyl)methanesulfonamide → HCID 46896574, compound

HRID 1046539Notes

Reaction equation

HRID 1046539 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.[NH2:25][CH:26]1[CH2:31][CH2:30][CH:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28][CH2:27]1>CN1C(=O)CCC1.O>[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]([NH:25][CH:26]4[CH2:31][CH2:30][CH:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28][CH2:27]4)[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

Participants

5

Reactant 2

HCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 86660233HCID 86660233, compound

Product 1

HCID 46896574HCID 46896574, compoundYield 9.6%

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 (0.1 g), N-(4-amino-cyclohexyl)-methanesulfonamide (0.2 g), and TEA (0.21 mL) in NMP (2 mL) was stirred at 100° C. overnight. 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 2× using 100% DCM to 15% MeOH/DCM. Pure fractions were collected, concentrated, and titurated with EtOAc. The resulting solid was filtered and dried at 50° C. under vacuum overnight to provide N-{4-[4-(8-benzyloxy-imidazo[1,2-a]pyridin-3-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanesulfonamide (compound 7, 14 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 2×
  6. customPure fractions were collected
  7. concentrationconcentrated
  8. filtrationThe resulting solid was filtered
  9. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-551680803bd2427abbe18f943ae623de
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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