1,1'-Carbonyldiimidazole → HCID 86700508, compound

HRID 1500519Notes

Reaction equation

HRID 1500519 reaction equation
[Br:1][C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][C:5]([NH2:13])=[C:4]([Cl:14])[CH:3]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:45][CH2:44][N:43]([C:20](=[O:21])[NH:13][C:5]3[CH:6]=[C:7]([O:8][C:9]([F:11])([F:12])[F:10])[C:2]([Br:1])=[CH:3][C:4]=3[Cl:14])[CH2:42][CH2:41]2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 17750358tert-Butyl 4-(piperazin-1-yl)piperidine-1-carboxylateHCID 674959584-Bromo-2-chloro-5-(trifluoromethoxy)benzenamine

Product 1

HCID 86700508HCID 86700508, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-chloro-5-trifluoromethoxy-phenylamine (0.55 g, 1.90 mmol) in DCM (4.9 mL) was added CDI (0.34 g, 2.09 mmol). The reaction solution was stirred at RT overnight and then 4-piperazin-1-yl-piperidine-1-carboxylic acid tert-butyl ester (0.56 g, 2.09 mmol; Preparation 12) was added and the reaction mixture was stirred for 30 min at RT, concentrated under vacuum and purified by silica gel chromatography (0-5% MeOH/DCM). Pure fractions were combined and concentrated under vacuum to provide the title intermediate (0.67 g, 60% yield) as a white foam. (m/z): [M+H]+ calcd for C22H29BrClF3N4O4 585.1 found 584.6.

Workup

  1. stirringthe reaction mixture was stirred for 30 min at RT
  2. concentrationconcentrated under vacuum
  3. custompurified by silica gel chromatography (0-5% MeOH/DCM)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7a62b28906284bb899b968304a7e75bc
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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