1,1'-Carbonyldiimidazole → HCID 22632914, compound

HRID 2270216Notes

Reaction equation

HRID 2270216 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C:12]1[C:13]([NH:24][CH:25]2[CH2:27][CH2:26]2)=[N:14][C:15]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:16]([F:18])[CH:17]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[O:29]>C(Cl)(Cl)Cl>[CH2:1]([O:8][N:9]1[C:10](=[O:11])[C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[N:14][C:13]=2[N:24]([CH:25]2[CH2:27][CH2:26]2)[C:28]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 54236381HCID 54236381, compound

Product 1

HCID 22632914HCID 22632914, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-benzyloxy-2-cyclopropylamino-5-fluoro-6-pyrrolidinyl-3-pyridinecarboxamide (Example I-2, 155 mg, 0.44 mmol) and 1,1′-carbonyldiimidazole (CDI) (142 mg, 0.88 mmol) in chloroform (2 mL) was refluxed overnight. The mixture was concentrated and purified by flash chromatography on a silica gel column with dichloromethane as eluent giving 130 mg of the title compound as a solid, mp 184-186° C.

Workup

  1. customwas refluxed overnight
  2. concentrationThe mixture was concentrated
  3. custompurified by flash chromatography on a silica gel column with dichloromethane as eluent

Sources & evidence

ORD record
ord-710229413fa54061b20b49f361128bdc
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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