Cesium carbonate → (R,E)-1-(3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 571387Notes

Reaction equation

HRID 571387 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8](/[CH:30]=[CH:31]/[CH2:32][O:33][CH3:34])=[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:35]1([C@H:41]([NH:43][C:44]([NH2:46])=[O:45])[CH3:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>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+].CC(N(C)C)=O>[CH3:34][O:33][CH2:32]/[CH:31]=[CH:30]/[C:8]1[C:5]2[CH:6]=[N:7][C:2]([NH:46][C:44]([NH:43][C@@H:41]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH3:42])=[O:45])=[CH:3][C:4]=2[N:10]([C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13013340(R)-1-(1-phenylethyl)ureaHCID 89525849(E)-6-chloro-3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 117601640(R,E)-1-(3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 2

HCID 25112666BrettPhos PalladacycleCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

(E)-6-chloro-3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (111 mg, 0.239 mmol), (R)-1-(1-phenylethyl)urea (59 mg, 0.359 mmol), Cs2CO3 (194 mg, 0.597 mmol), BrettPhos precatalyst (19.06 mg, 0.024 mmol) and DMA (1.5 ml). The mixture was evacuated and purged with nitrogen six times and heated at 100° C. for 35 min. The mixture was diluted with EtOAc and washed with water, brine, dried (Na2SO4) and concentrated to afford crude (R,E)-1-(3-(3-methoxyprop-1-en-1-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea, which was used in the next step. MS ESI calc'd. for C38H36N5O2 [M+H]+ 594, found 594.

Workup

  1. customThe mixture was evacuated
  2. custompurged with nitrogen six times
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5991a3bd6b634ecdbe006c6e84bb467c
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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