Cesium carbonate → HCID 68312931, compound

HRID 1530439Notes

Reaction equation

HRID 1530439 reaction equation
C(OC(N1CCC(C([O:20][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)CC)CC1)=O)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:50]([O:57][C:58](=[O:72])[C:59](Br)([CH3:70])[CH2:60][CH2:61][O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CC#N>[CH2:50]([O:57][C:58](=[O:72])[C:59]([O:20][C:21]1[CH:43]=[CH:42][C:24]2[C:25]3[N:29]([CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1)[CH:28]=[C:27]([C:33]1[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=1)[N:26]=3)([CH3:70])[CH2:60][CH2:61][O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68312705HCID 68312705, compoundHCID 68312814HCID 68312814, compound

Product 1

HCID 68312931HCID 68312931, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (100 mg, 0.307 mmol) and Cs2CO3 (200 mg, 0.615 mmol) in CH3CN (1 mL) was added a solution of 4-benzyloxy-2-bromo-2-methylbutyric acid benzyl ester (0.345 mmol) in CH3CN (7 mL) and stirring at reflux temperature was continued for 3 h. After cooling to RT, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM) affording 4-Benzyloxy-2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylbutyric acid benzyl ester as a pale orange gum (36 mg, 19%). LCMS: RT 4.28 min [M+H]+ 622.3

Workup

  1. temperatureat reflux temperature
  2. customthe reaction mixture was partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM)

Sources & evidence

ORD record
ord-057e103b03c24c898a0a58b7d90497d5
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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