1,1'-Carbonyldiimidazole → HCID 69157387, compound

HRID 967393Notes

Reaction equation

HRID 967393 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[CH2:34][NH2:35])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CC#N.C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:27]3[C:28](=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[CH2:34][NH:35][C:1]2=[O:2])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 69157348HCID 69157348, compound

Product 1

HCID 69157387HCID 69157387, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

1,1′-Carbonyldiimidazole (0.51 g, 3.15 mmol) was added to a solution of 4-(2-aminomethyl-4-chloro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.79 g, 2.25 mmol) in CH3CN (10 mL) over 3 h with stirring at 50° C. The reaction mixture was then cooled to room temperature and stirred for additional 2 h. The reaction mixture was dissolved in CH2Cl2 (100 mL), washed with water (2×10 mL), brine (1×10 mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, 30-50% EtOAc/hexanes) to obtain 0.46 g (63%) of the desired product. TLC (silica, 50% EtOAc/hexanes): Rf=0.5. MS (electrospray): exact mass calculated for C18H24ClN3O3, 365.15. m/z found, 388.1 [M++Na]. 1H NMR (CDCl3, 400 MHz): 7.18 (dd, J=6.26 Hz, 2.54 Hz, 1H), 7.05 (d, J=2.15 Hz, 1H), 6.94 (d, J=9.00 Hz, 1H), 6.29 (s, 1H), 4.32-4.18 (m, 4H), 4.13-4.02 (m, 1H), 2.88-2.71 (m, 2H), 2.64-2.50 (m, 2H), 1.82-1.73 (m, 2H), 1.49 (s, 9H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringstirred for additional 2 h
  3. washwashed with water (2×10 mL), brine (1×10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, 30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f9bd7afc01454b95b340818735e8ee47
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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