Potassium Iodide → HCID 68800627, compound

HRID 238228Notes

Reaction equation

Br[CH:2]([C:4]1[N:13]([CH3:14])[C:12](=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([NH:16][CH:2]([C:4]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH3:3])[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-(1-bromo-ethyl)-3-methyl-3H-quinazolin-4-one (801 mg, 3 mmol), 4-amino-1-N-Boc piperidine (661 mg, 3.3 mmol), potassium iodide (498 mg, 3 mmol) and potassium carbonate (622 mg, 4.5 mmol) in acetonitrile (12 mL) was heated at 65° C. for 3 days. The reaction mixture was then concentrated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium thiosulphate solution and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to yield 4-[1-(3-Methyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester (HPLC ret. time 2.20, 10-99% CH3CN, 5 min run, ESI-MS m/z 387.4 (MH+).

Workup

concentrationThe reaction mixture was then concentrated in vacuo
dissolutionThe residue was dissolved in dichloromethane
washwashed with saturated sodium thiosulphate solution and water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dee036ede34548e996bcb3bc2996c22f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642609B2

Reaction notes

Loading…