1,1'-Carbonyldiimidazole → HCID 178522617, compound

HRID 2280419Notes

Reaction equation

HRID 2280419 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[CH2:4][NH:5]/[C:6](/[NH:18][C:19]1[NH:23][N:22]=[C:21]([C:24]([F:27])([F:26])[F:25])[CH:20]=1)=[N:7]/[C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>C1COCC1>[Cl:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[C:33](=[O:34])[N:23]2[N:22]=[C:21]([C:24]([F:25])([F:26])[F:27])[CH:20]=[C:19]2[NH:18]/[C:6]/1=[N:7]\[C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[CH:10]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178523897HCID 178523897, compound

Product 1

HCID 178522617HCID 178522617, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)—N-(((2-chloro-4-fluorobenzyl)amino)((3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)methylene)-3,4-difluorobenzamide (50 mg, 0.11 mmol) in THF (1 mL) was added 1,1′-carbonyldiimidazole (CDI) (26 mg, 0.16 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Purification by silica chromatography (EtOAc:hexanes) provided the title compound (14 mg, 27% yield). HPLC (Method A): 11.1 min.

Workup

  1. customPurification by silica chromatography (EtOAc:hexanes)

Sources & evidence

ORD record
ord-5f067f000d0c49a6a1c116e9b3411d88
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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