tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 22647998, compound

HRID 394192Notes

Reaction equation

HRID 394192 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][N:21]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)[C:22](=[O:34])[N:23]2[C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])=[C:18]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[Cl:50])[CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:18]1[CH:17]=[C:16]([NH:15][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH:25]=[C:24]2[C:19]=1[CH2:20][N:21]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)[C:22](=[O:34])[N:23]2[C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 226480157-amino-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 22647998HCID 22647998, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-butyl 4-oxopiperidine-1-carboxylate (37.9 mg, 0.19 mmol) was added to a mixture of 7-amino-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one (78 mg, 0.15 mmol) in 1 mL of 1,2-dichloroethane. NaBH(OAc)3 (58 mg, 0.27 mmol) was added after 45 min. The reaction mixture was stirred at rt overnight. The reaction mixture was quenched with ca 5 mL of 2.5M aqueous NaOH, extracted with (3×20 mL) of ethyl acetate, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The product was purified by preparative thin-layer chromatography, eluting with 90:10 hexanes-ethyl acetate to yield tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]amino}piperidine-1-carboxylate. Mass spectrum (ESI) 721.2 (M+1).

Workup

  1. customThe reaction mixture was quenched with ca 5 mL of 2.5M aqueous NaOH
  2. extractionextracted with (3×20 mL) of ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by preparative thin-layer chromatography
  7. washeluting with 90:10 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-1c572e4d8db046a482539663e341d187
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…