HCID 45257321, compound → HCID 178501345, compound

HRID 656591Notes

Reaction equation

HRID 656591 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[C:11](=S)[NH:10][C@@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[CH2:8][C:6]=2[N:7]=1.[NH2:22][O:23][C@H:24]1[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:26]([C:36]([O:38][CH3:39])=[O:37])[CH2:25]1>[Hg](OC(C)=O)OC(C)=O.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2=[C:6]([CH2:8][C@H:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[Br:20])[NH:10]/[C:11]/2=[N:22]\[O:23][C@H:24]2[CH2:28][N:27]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[C@H:26]([C:36]([O:38][CH3:39])=[O:37])[CH2:25]2)[N:7]=1

Participants

5

Reactant 2

HCID 45257321HCID 45257321, compoundHCID 57999148(2S,4R)-1-tert-butyl 2-methyl 4-(aminooxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 178501345HCID 178501345, compoundYield 570%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-5(6H)-thione (150 mg, 0.4 mmol), (2S,4R)-1-tert-butyl 2-methyl 4-(aminooxy)pyrrolidine-1,2-dicarboxylate (416 mg, 1.6 mmol), Hg(OAc)2 (256 mg, 0.8 mmol) and toluene (2 mL) was heated at 100° C. for 2 h. Cooled to rt, filtered through celite and purified to afford (2S,4R)-1-tert-butyl 2-methyl 4-((Z)—((R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylidene)aminooxy)pyrrolidine-1,2-dicarboxylate (172 mg, 570%) as off white solid. MS (ES) [M+H] calculated for C25H31BrFN6O5, 593.14. found 593.10.

Workup

  1. temperatureCooled to rt
  2. filtrationfiltered through celite
  3. custompurified

Sources & evidence

ORD record
ord-24be41d3ab3a4d25b542befd11cf2141
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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