Cesium carbonate → HCID 178433342, compound

HRID 1917517Notes

Reaction equation

HRID 1917517 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:22])[C:5]2=[C:6]([CH2:8][C@H:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[Br:21])[NH:10]/[C:11]/2=[N:12]\[OH:13])[N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:30]1[CH2:34][CH2:33][O:32][C:31]1=[O:35]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:22])[C:5]2=[C:6]([CH2:8][C@H:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[Br:21])[NH:10]/[C:11]/2=[N:12]\[O:13][CH:30]2[CH2:34][CH2:33][O:32][C:31]2=[O:35])[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 178433358HCID 178433358, compound

Product 1

HCID 178433342HCID 178433342, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R,Z)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one oxime (0.3 mmol, 109 mg) in DMF (2.0 mL) was added Cs2CO3 (0.45 mmol, 146 mg) and 3-bromodihydrofuran-2(3H)-one (0.36 mmol, 33.6 μL). The reaction mixture was stirred overnight at r.t. and LCMS shows completion of the reaction. The reaction mixture was poured on crushed ice and the resultant solid was filtered and dried to afford 3-((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)dihydrofuran-2(3H)-one (105 mg, 78%) as off white solid. MS (ES). [M+H] calculated for C18H18BrFN5O3, 450.05; found 450.30.

Workup

  1. customcompletion of the reaction
  2. additionThe reaction mixture was poured
  3. customon crushed ice
  4. filtrationthe resultant solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-d6ecadd5c53d4f6f9ac0d7f2f476a1bf
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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