Cesium carbonate → HCID 68313011, compound

HRID 1530443Notes

Reaction equation

HRID 1530443 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:52][C:53](=[O:64])[CH:54](Br)[CH2:55][CH:56]([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH3:51]>CC#N>[CH2:50]([O:52][C:53](=[O:64])[CH:54]([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)[CH2:55][CH:56]([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH3:51]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68312705HCID 68312705, compoundHCID 86671456HCID 86671456, compound

Product 1

HCID 68313011HCID 68313011, compoundYield 73.4%

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 (330 mg, 1.013 mmol) in CH3CN (18 mL) was added Cs2CO3 (825 mg, 2.53 mmol) followed by a solution of 2-bromo-4-methylpentanedioic acid diethyl ester (640 mg, 2.276 mmol) in CH3CN (2 mL) and stirring at reflux temperature was continued for 1.5 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 2-8% MeOH in DCM) affording 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]-4-methylpentanedioic acid diethyl ester as a pale yellow gum (391 mg, 73%). LCMS: RT 3.59 min [M+H]+ 526.5

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 2-8% MeOH in DCM)

Sources & evidence

ORD record
ord-52f5f05338ef470a842997d0b0f9dc53
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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