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

HRID 588176Notes

Reaction equation

HRID 588176 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([O:30][CH3:31])=[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:32]1([C@H:38]([NH:40][C:41]([NH2:43])=[O:42])[CH3:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.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.O1CCOCC1>[CH3:31][O:30][C:8]1[C:5]2[CH:6]=[N:7][C:2]([NH:43][C:41]([NH:40][C@@H:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH3:39])=[O:42])=[CH:3][C:4]=2[N:10]([C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 13013340(R)-1-(1-phenylethyl)ureaHCID 25112535BrettphosHCID 1182718976-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 118271885(R)-1-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 2

HCID 25112535BrettphosCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (133 mg, 0.312 mmol), (R)-1-(1-phenylethyl)urea (115 mg, 0.700 mmol), 1:1 BrettPhos:BrettPhos pre-catalyst (20.5 mg, 0.015 mmol), and cesium carbonate (254 mg, 0.781 mmol) were taken up in 1,4-dioxane (3 mL) in a 5 mL microwave vial. The vial was evacuated and back-filled with N2 (×3) and the reaction stirred at 100° C. for 6 h. The reaction mixture was filtered through Celite, eluting with MeOH, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (12-100% EtOAc-hexanes) gave (R)-1-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C35H31N5O2 [M+1]+ 554. found 554.

Workup

  1. customThe vial was evacuated
  2. additionback-filled with N2 (×3)
  3. filtrationThe reaction mixture was filtered through Celite
  4. washeluting with MeOH
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash chromatography (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-25b5ac2866c24d118599962a10a91a80
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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