Triethylamine → HCID 68781645, compound

HRID 2264458Notes

Reaction equation

HRID 2264458 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>CN1C(=O)CCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:2]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([Cl:18])[CH:8]=3)[N:3]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 86615298HCID 86615298, compound

Product 1

HCID 68781645HCID 68781645, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2,6-dichloro-4-morpholin-4-yl-quinazoline (0.9 g, 3.17 mmol, 1.0 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.27 g, 6.33 mmol, 2.0 equiv; commercially available) in anhydrous NMP (8 mL) and triethylamine (2 mL) was heated by microwave irradiation to 170° C. for 1 h. 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 toluene/ethyl acetate (4:1→2:1) providing 0.6 g (42%) of the title compound. MS (ISP): 448.3 [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 toluene/ethyl acetate (4:1→2:1)

Sources & evidence

ORD record
ord-d772cb1f10ac43198d843bdd16203789
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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