Cesium carbonate → HCID 68312961, compound

HRID 1530421Notes

Reaction equation

HRID 1530421 reaction equation
C(OC(N1CC[CH:14]([CH:17]([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)[CH2:18]C)CC1)=O)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:50][O:51][C:52](=[O:57])C(Br)(C)C>CC#N>[CH3:50][O:51][C:52](=[O:57])[C:17]([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)([CH3:18])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 68312705HCID 68312705, compound

Product 1

HCID 68312961HCID 68312961, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture 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 (30 mg, 0.0922 mmol), Cs2CO3 (75 mg, 0.23 mmol) and 2-bromo-2-methylpropionic acid methyl ester (36 uL, 0.277 mmol) in CH3CN (2 mL) was heated at reflux temperature for 2 h. After cooling to RT, the mixture was partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc and the combined organic layers were washed with 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]-2-methylpropionic acid methyl ester as a colorless gum (40 mg, quantitative). LCMS: RT 3.25 min [M+H]+ 426.1

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. customthe mixture was partitioned between EtOAc and water
  4. extractionThe aqueous layer was further extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% MeOH in DCM)

Sources & evidence

ORD record
ord-22e01c05f8544343accbc4744fcb68e1
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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