Cesium carbonate → ethyl 3-(6-(3-benzylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate

HRID 571417Notes

Reaction equation

HRID 571417 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:43]([NH:50][C:51]([NH2:53])=[O:52])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].O1CCOCC1>[CH2:43]([NH:50][C:51](=[O:52])[NH:53][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 10853BenzylureaHCID 89525821ethyl 3-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate

Product 1

HCID 89525900ethyl 3-(6-(3-benzylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoateYield 53.4%

Reagents, catalysts & solvents 2

HCID 25112666BrettPhos PalladacycleCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

An oven-dried, nitrogen cooled 2 ml microwave vial was charged with ethyl 3-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate (59 mg, 0.119 mmol), BrettPhos precatalyst (5 mg, 6.26 μmol), cesium carbonate (122 mg, 0.374 mmol) and 1-benzylurea (32 mg, 0.213 mmol), sealed under a nitrogen atmosphere, charged with Dioxane (0.5 ml) and heated to 100° C. for 16 hr. Filtered through celite, eluted with EtOAc, concentrated in vacuo and purified via flash chromatography (0-20% MeOH/DCM) to provide ethyl 3-(6-(3-benzylureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)propanoate (38.7 mg, 0.063 mmol, 53.4% yield) as a yellow solid. MS ESI calc'd for C38H35N5O3 [M+H]+=610, found 610.

Workup

  1. temperatureAn oven-dried, nitrogen cooled 2 ml microwave vial
  2. customsealed under a nitrogen atmosphere
  3. filtrationFiltered through celite
  4. washeluted with EtOAc
  5. concentrationconcentrated in vacuo
  6. custompurified via flash chromatography (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-3ea327cda3d54d85ae65db47a1f652e0
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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