Cesium carbonate → HCID 68313044, compound

HRID 1530371Notes

Reaction equation

HRID 1530371 reaction equation
C(OC(N1CCC(C(O[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.[CH2:44]([O:51][C:52]([N:54]1[CH2:59][CH2:58][CH:57]([CH:60]([O:65]S(C(F)(F)F)(=O)=O)[C:61]([F:64])([F:63])[F:62])[CH2:56][CH2:55]1)=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:44]([O:51][C:52]([N:54]1[CH2:59][CH2:58][CH:57]([CH:60]([O:65][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)[C:61]([F:64])([F:63])[F:62])[CH2:56][CH2:55]1)=[O:53])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68312705HCID 68312705, compoundHCID 86671454HCID 86671454, compound

Product 1

HCID 68313044HCID 68313044, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 (300 mg, 0.92 mmol), 4-(2,2,2-trifluoro-1-trifluoromethanesulfonyloxyethyl)piperidine-1-carboxylic acid benzyl ester (870 mg, 2.1 mmol) and Cs2CO3 (680 mg, 2.1 mmol) were suspended in DMF (5 mL), stirred at RT for 2 h and then heated at 80° C. for 18 h. The reaction mixture was then quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc) affording the title compound (210 mg, 37%). LCMS: RT 4.04 min [M+H]+ 625.0.

Workup

  1. temperatureheated at 80° C. for 18 h
  2. customThe reaction mixture was then quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-bff8f09ba4b84431b233f149596d6a72
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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