Cesium carbonate → HCID 118271680, compound

HRID 590802Notes

Reaction equation

HRID 590802 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([NH2:30])=[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:31]1([C@H:37]([NH:39][C:40]([NH2:42])=[O:41])[CH3:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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+].O1CCOCC1>[NH2:30][C:8]1[C:5]2[CH:6]=[N:7][C:2]([NH:42][C:40]([NH:39][C@@H:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:38])=[O:41])=[CH:3][C:4]=2[N:10]([C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13013340(R)-1-(1-phenylethyl)ureaHCID 118272274HCID 118272274, compound

Product 1

HCID 118271680HCID 118271680, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 25112666BrettPhos PalladacycleCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (500 mg, 1.217 mmol), (R)-1-(1-phenylethyl)urea (400 mg, 2.434 mmol), cesium carbonate (1023 mg, 3.14 mmol) and chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-i-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (58.3 mg, 0.073 mmol) were charge in a 40 mL vial with dioxane (11 ml). System was degassed and stirred at 100° C. for 3 hours. Reaction mixture was evaporated in vacuo and purified by normal phase column chromotography eluting with hexane/EtOAc (0-50%) affording (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (333 mg, 0.618 mmol, 50.8% yield) as an off white solid. 1H NMR (500 MHz, dmso) δ 8.82 (s, 1H), 8.51 (s, 1H), 8.32 (bs, 1H), 7.38-7.13 (m, 19H), 6.49 (s, 1H), 5.88 (s, 2H), 4.85-4.75 (m, 1H), 1.35 (d, 3H). MS ESI calc'd. For C34H30N6O[M+H]+ 539. found 539.

Workup

  1. customSystem was degassed
  2. customReaction mixture
  3. customwas evaporated in vacuo
  4. custompurified by normal phase column chromotography
  5. washeluting with hexane/EtOAc (0-50%)

Sources & evidence

ORD record
ord-b62aa66ed43e412ab2eb665c8769b84b
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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