Cesium carbonate → HCID 22609270, compound

HRID 2306573Notes

Reaction equation

HRID 2306573 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]1[C:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[N:16][N:17]=[C:10]1[N:9]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:8]2=[O:30])(=[O:3])[CH3:2].[CH2:31](Br)[CH:32]=CC1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(NC1C=C2C(=CC=1)N1C(N3CCCC3)=NN=C1NC2=O)(=O)C.CN(C=O)C.[Pd]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]1[C:15]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)=[N:16][N:17]=[C:10]1[N:9]([CH2:23]/[CH:24]=[CH:29]/[C:28]1[CH:27]=[CH:26][CH:25]=[CH:32][CH:31]=1)[C:8]2=[O:30])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 98116BromomethylstyreneHCID 22609258HCID 22609258, compound

Product 1

HCID 22609270HCID 22609270, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 136388390HCID 136388390, compoundSolvent

Procedure

From 1.2 g (3.0 mmol) of 7-acetamido-4-benzyl-1-(pyrrolidin-1yl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (described in example 221) debenzylated in 7-acetamido-1-(pyrrolidin-1yl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one by Palladium/C method described in example 257, then directly treated with 0.59 g of cinnamyl bromide in the presence of 0.98 g cesium carbonate, in 15 ml of DMF, according to a method described in example 3. We obtain, after purification by chromatography on silica column and recrystallization in ethanol, 0.4 g of pure compound from example 222.

Workup

  1. customWe obtain
  2. customafter purification by chromatography
  3. customon silica column and recrystallization in ethanol

Sources & evidence

ORD record
ord-7fbc7ca8b6cb4a5888592d5cd6edc353
Source dataset
uspto-grants-2004_12
Patent number
US06828315B1

Reaction notes

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