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Potassium Iodide → HCID 68800627, compound

HRID 238228
Notes
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Reaction equation

HRID 238228 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 59993195HCID 59993195, compound

Product 1

HCID 68800627HCID 68800627, compound

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

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

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium thiosulphate solution and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes