Potassium Carbonate → HCID 10166710, compound

HRID 1250224Notes

Reaction equation

HRID 1250224 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH2:7][C:8]2[N:17]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:16](=[O:27])[C:15]3[C:10](=[C:11]([O:28][CH3:29])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:17]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:34][CH2:35][CH2:36][N:37]4[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]4)[CH2:23][CH2:22]3)[C:16](=[O:27])[C:15]3[C:10](=[C:11]([O:28][CH3:29])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 10299353HCID 10299353, compound

Product 1

HCID 10166710HCID 10166710, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 2-(4-chloro-phenoxymethyl)-8-methoxy-3-(3-piperidin-4-yl-propyl)-3H-quinazolin-4-one (150 mg, 0.31 mmol), N-(3-chloropropyl)-piperidine hydrochloride (222 mg, 0.63 mmol), K2CO3 (87 mg, 0.63 mmol), Kl (105 mg, 0.63 mmol) was heated at 80° C. in THF/H2O (3:1 mixture, 30 mL) for 17 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc. The organic solution was separated and was washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated. The crude residue was chromatographed on SiO2-gel using EtOAc/NEt3 (10:1) to give the desired product as an oil. API-MS: 567.2 (M+1). 1H NMR (300 MHz, d4-MeOH): d 7.75 (d, 1 H), 7.5 (t,1 H), 7.38 (d, 1 H), 7.3 (d, 2 H), 7.1 (d, 2 H), 5.25 (s, 2 H), 4.1 (m, 2 H), 4.0 (s, 3 H), 2.9 (m), 2.4-2.1 (m), 1.9-1.1 (m).

Workup

  1. customThe organic solution was separated
  2. washwas washed with sat'd aq NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. customThe crude residue was chromatographed on SiO2-gel

Sources & evidence

ORD record
ord-74009650a6ae4fd2b87cde1e85025f80
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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