1,1'-Carbonyldiimidazole → 1-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one

HRID 523465Notes

Reaction equation

HRID 523465 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[CH:13]1([NH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[NH2:23])[CH2:15][CH2:14]1>CC#N>[CH:13]1([N:16]2[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[NH:23][C:6]2=[O:7])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 191025534-N-cyclopropylpyridine-3,4-diamine

Product 1

HCID 223493611-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

CDI (CAS 530-62-1) (151.8 g, 936 mmol) was added to a solution of the intermediate 5-c (133 g, 891.4 mmol) in CH3CN (1800 mL) at 0° C. The reaction was allowed to warm to 10° C. and stirred for 1 hour. The solid was collected by filtration, then washed with CH3CN (200 mL) to afford compound 5-d as a white powder (101 g, 65%).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with CH3CN (200 mL)
  3. customto afford compound 5-d as a white powder (101 g, 65%)

Sources & evidence

ORD record
ord-b2e1507672b34560aeead35047c16c37
Source dataset
uspto-grants-2016_05
Patent number
US09339494B2

Reaction notes

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