Hydrochloric Acid → HCID 178510283, compound

HRID 1370112Notes

Reaction equation

HRID 1370112 reaction equation
[NH2:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].[OH-].[Na+].Cl>C(#N)C>[C:8]([C:6]1[CH:7]=[C:2]2[NH:1][C:18](=[O:19])[N:10]([C@H:11]3[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]3)[C:3]2=[N:4][CH:5]=1)#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 178510356HCID 178510356, compound

Product 1

HCID 178510283HCID 178510283, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-amino-5-cyano-2-(trans-4-hydroxycyclohexylamino)pyridine (3.1 g) and 1,1′-carbonyldiimidazole (6.49 g) in acetonitrile (31 mL) was stirred at 50° C. under nitrogen atmosphere for 15 minutes. After adding 1N-NaOH(35 mL), the mixture was stirred at 60° C. for 1.5 hours. The reaction mixture was neutralized with concentrated hydrochloric acid to yield a precipitate. The resulting precipitate was collected by filtration and washed successively with water and aqueous ethanol to give 6-cyano-3-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (1.93 g) as a brown solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for 1.5 hours
  2. customto yield a precipitate
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed successively with water and aqueous ethanol

Sources & evidence

ORD record
ord-bad1eea8924c45308513e6dba8d5d3ec
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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