4-Amino-1-Boc-piperidine → HCID 68781498, compound

HRID 2264454Notes

Reaction equation

HRID 2264454 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:19])[CH:8]=2)[N:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN1C(=O)CCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([NH:33][C:2]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:19])[CH:8]=3)[N:3]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 132061322,6-Dichloro-4-(2-fluorophenyl)quinazoline

Product 1

HCID 68781498HCID 68781498, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2,6-dichloro-4-(2-fluoro-phenyl)-quinazoline (0.92 g, 3.14 mmol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.82 g, 4.08 mmol, 1.3 equiv; commercially available) in anhydrous NMP (8 mL) was heated by microwave irradiation to 180° C. for 40 min. The organic phase was concentrated under reduced pressure and the residue extracted with dichloromethane (3×50 mL) from a sat. solution of sodium bicarbonate (100 mL). The combined organic phases were dried over MgSO4 and the product purified by column chromatography on silica eluting with a gradient of heptane/ethyl acetate (6:1 h 1:1) providing 0.66 g (66%) of the title compound. MS (ISP): 457.4 [M+H]+.

Workup

  1. concentrationThe organic phase was concentrated under reduced pressure
  2. extractionthe residue extracted with dichloromethane (3×50 mL) from a sat. solution of sodium bicarbonate (100 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe product purified by column chromatography on silica eluting with a gradient of heptane/ethyl acetate (6:1 h 1:1)

Sources & evidence

ORD record
ord-741fb5fd2e8c4fe4bfb863e527e1fa2f
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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