Cesium carbonate → HCID 118271674, compound

HRID 590851Notes

Reaction equation

HRID 590851 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[N:12]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[C:8]3[C:9]2=[C:4]([CH2:5][CH2:6][N:7]3[CH:33]([CH3:35])[CH3:34])[N:3]=1.[C:36]1([C@H:42]([NH:44][C:45]([NH2:47])=[O:46])[CH3:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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.C(Cl)Cl>[CH:33]([N:7]1[CH2:6][CH2:5][C:4]2[N:3]=[C:2]([NH:47][C:45]([NH:44][C@@H:42]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH3:43])=[O:46])[CH:11]=[C:10]3[N:12]([C:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:13]=[C:8]1[C:9]=23)([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13013340(R)-1-(1-phenylethyl)ureaHCID 118272360HCID 118272360, compound

Product 1

HCID 118271674HCID 118271674, compound

Reagents, catalysts & solvents 2

HCID 25112535BrettphosCatalystHCID 6344DichloromethaneSolvent

Procedure

7-chloro-3-isopropyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridine (116 mg, 0.242 mmol), (R)-1-(1-phenylethyl)urea (60 mg, 0.363 mmol), cesium carbonate (237 mg, 0.726 mmol) and BrettPhos pre-catalyst (22 mg, 0.024 mmol) were charged in a 1 dram vial, evacuated and backfilled with nitrogen and taken in 1,4-dioxane (1.2 mL) before the mixture was heated reaction at 100° C. for 1 hour. The reaction mixture was diluted with DCM, washed with water, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-75% EtOAc-hexanes) gave (R)-1-(3-isopropyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C39H38N6O [M+H]+ 607. found 607.

Workup

  1. customevacuated
  2. temperaturewas heated
  3. customreaction at 100° C. for 1 hour
  4. washwashed with water, brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the residue by flash column (0-75% EtOAc-hexanes)

Sources & evidence

ORD record
ord-e9f77326f76f4d0dbc2dbdd462cd79c1
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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