HCID 68523091, compound → HCID 59511763, compound

HRID 1157473Notes

Reaction equation

HRID 1157473 reaction equation
[C:1]([NH:5][C:6](=[O:35])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:19]=[CH:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[N:10]=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([NH:5][C:6](=[O:35])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[N:10]=[C:9]1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68523091HCID 68523091, compound

Product 1

HCID 59511763HCID 59511763, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-tert-butyl-2-[2-(3-chlorophenyl)-4-oxo-6-(4-pyrrolidin-1-ylbut-1-enyl)-4H-quinazolin-3-yl]acetamide (EXAMPLE 10a) (303 mg, 0.62 mmol) in dry methanol (6 mL) was sparged (5 min) with argon, and 10% Pd/C (24 mg, catalytic) was added. The reaction mixture was stirred under a hydrogen atmosphere(1 atm.) for 4 h at room temperature. The mixture was filtered through CELITE™, and the filter cake was washed with methanol (3×10 mL). The filtrates were evaporated under reduced pressure to afford N-tert-butyl-2-[2-(3-chlorophenyl)-4-oxo-6-(4-pyrrolidin-1-ylbutyl)-4H-quinazolin-3-yl]acetamide (EXAMPLE 11a) (223 mg, 0.45 mmol, 73%) as yellow foam.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through CELITE™
  3. washthe filter cake was washed with methanol (3×10 mL)
  4. customThe filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-23b9d936826340e3a0b8fc496502967c
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

Loading…