1,1'-Carbonyldiimidazole → HCID 86700514, compound

HRID 1500524Notes

Reaction equation

HRID 1500524 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][N:37]([CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[C@@H:36]([CH3:46])[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][N:37]([CH: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)[C@@H:36]([CH3:46])[CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 674959584-Bromo-2-chloro-5-(trifluoromethoxy)benzenamineHCID 86700515HCID 86700515, compound

Product 1

HCID 86700514HCID 86700514, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-2-chloro-5-trifluoromethoxy-phenylamine (92.5 mg, 0.32 mmol) in DCM (0.82 mL) was added CDI (56.8 mg, 0.35 mmol). The reaction mixture was stirred at RT for 6 h and a solution of (S)-3-methyl-4-piperidin-4-yl-piperazine-1-carboxylic acid tert-butyl ester (99.3 mg, 0.35 mmol; Preparation 22) in DCM (1 mL) was added. The solution was concentrated under vacuum and purified by silica gel chromatography (0-5% MeOH/DCM). Product fractions were combined and concentrated under vacuum to provide the title intermediate (32 mg, 17% yield) as a clear oil. (m/z): [M+H]+ calcd for C23H31BrClF3N4O4 599.12, 601.11 found 601.4.

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. custompurified by silica gel chromatography (0-5% MeOH/DCM)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6ff51f7788b347548a1b611443995228
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

Loading…