HCID 70981488, compound → HCID 70979908, compound

HRID 1749084Notes

Reaction equation

HRID 1749084 reaction equation
[C:1]([O:5][C:6](=[O:43])[N:7]([C:19]1[CH:20]=[CH:21][C:22]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30](Cl)[CH:29]=3)[C:26](=[O:35])[C:25]([CH3:41])([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[O:24][C:23]=2[N:42]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:43])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])[C:19]1[CH:20]=[CH:21][C:22]2[N:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:26](=[O:35])[C:25]([CH3:41])([CH2:36][CH2:37][CH:38]([CH3:39])[CH3:40])[O:24][C:23]=2[N:42]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 70981488HCID 70981488, compound2×

Product 1

HCID 70979908HCID 70979908, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[1-(3-Chloro-phenyl)-3-methyl-3-(3-methyl-but-2-enyl)-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (Intermediate A3) (360 mg, 0.59 mmol) was dissolved in MeOH (20 mL) and stirred at ambient temperature for 16 hours in the presence of Pd/C (10%, 63 mg) under H2. The resulting suspension was filtered through Celite and the solvent was removed in vacuo to give (2,4-dimethoxy-benzyl)-[3-methyl-3-(3-methyl-butyl)-2-oxo-1-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl]-carbamic acid tert-butyl ester as a pale yellow solid (120 mg). MS: [M+H]+=576.

Workup

  1. filtrationThe resulting suspension was filtered through Celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-61356bd560024e16aa6d0377b98ba31e
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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