Triethylamine → HCID 68778514, compound

HRID 2264450Notes

Reaction equation

HRID 2264450 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[CH:8]=[C:7]3[O:13][CH2:14][O:15][C:6]3=[CH:5][C:4]=2[N:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>CN1C(=O)CCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:2]2[N:11]=[C:10]([NH2:12])[C:9]3[CH:8]=[C:7]4[O:13][CH2:14][O:15][C:6]4=[CH:5][C:4]=3[N:3]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 20556254HCID 20556254, compound

Product 1

HCID 68778514HCID 68778514, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 6-chloro-[1,3]dioxolo[4,5-g]quinazolin-8-ylamine (0.9 g, 4.02 mmol equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.61 g, 8.05 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 with column chromatography on silica eluting with a gradient of toluene/ethyl acetate (4:1→2:1) providing 0.6 g (39%) of the title compound. MS (ISP): 388.4 [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 with column chromatography on silica eluting with a gradient of toluene/ethyl acetate (4:1→2:1)

Sources & evidence

ORD record
ord-d5f1fa924ee0491ab42caf7713bad975
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

Loading…