Ammonium formate → 4-(3-{[3-(2-Tert-butoxy-2-oxoethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl]carbonyl}-2-methylindolizin-1-yl)benzoic acid

HRID 1502218Notes

Reaction equation

HRID 1502218 reaction equation
[C:1]([O:5][C:6](=[O:48])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([C:21]3[N:29]4[C:24]([CH:25]=[CH:26][CH:27]=[CH:28]4)=[C:23]([C:30]4[CH:45]=[CH:44][C:33]([C:34]([O:36]CC5C=CC=CC=5)=[O:35])=[CH:32][CH:31]=4)[C:22]=3[CH3:46])=[O:20])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:47])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CN(C=O)C.C(OC(C)C)(C)C>[C:1]([O:5][C:6](=[O:48])[CH2:7][N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([C:19]([C:21]3[N:29]4[C:24]([CH:25]=[CH:26][CH:27]=[CH:28]4)=[C:23]([C:30]4[CH:45]=[CH:44][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=4)[C:22]=3[CH3:46])=[O:20])=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:47])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 89657670Benzyl 4-(3-{[3-(2-tert-butoxy-2-oxoethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl]carbonyl}-2-methylindolizin-1-yl)benzoate

Product 1

HCID 1177763014-(3-{[3-(2-Tert-butoxy-2-oxoethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl]carbonyl}-2-methylindolizin-1-yl)benzoic acidYield 85.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolvent

Procedure

Palladium on carbon (10% active, 0.2 g) and benzyl 4-(3-{[3-(2-tert-butoxy-2-oxoethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl]carbonyl}-2-methylindolizin-1-yl)benzoate (1 g, 1.55 mmol) are added, under nitrogen, to ammonium formate (0.97 g, 15.54 mmol) in solution in 15 mL of DMF. The reaction mixture is stirred for 3 h at ambient temperature and filtered through Celite, and the filtrate is concentrated to dryness. The solid obtained is taken up in diisopropyl ether. After filtration and drying under vacuum, 732 mg (yield: 85%) of a green solid are obtained.

Workup

  1. filtrationfiltered through Celite
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe solid obtained
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-237ed4316b4d4650908423d2564a8ac4
Source dataset
uspto-grants-2015_12
Patent number
US09206177B2

Reaction notes

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