Cesium carbonate → HCID 118271680, compound

HRID 590804Notes

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.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

Conditions

Temperature: 100 °C

Procedure

6-Chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (5C; 4.0 g, 9.73 mmol), (R)-1-(1-phenylethyl)urea (2.4 g, 14.60 mmol), cesium carbonate (7.9 g, 24.34 mmol) and BrettPhos pre-catalyst (467 mg, 0.584 mmol) were charged in a 350 mL pressure vessel with 1.4-dioxane (88 mL). The system was degassed and stirred at 100° C. for 8 h. The reaction mixture was filtered through Celite, evaporated in vacuo, dissolved in DCM, and purified by flash chromatography (0-20% EtOAc/DCM) to afford (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C34H30N6O2 [M+1]+ 539. found 539.

Workup

customThe system was degassed
filtrationThe reaction mixture was filtered through Celite
customevaporated in vacuo
dissolutiondissolved in DCM
custompurified by flash chromatography (0-20% EtOAc/DCM)

Sources & evidence

ORD record: ord-6e68ff5ce25f40028cd8af3dfbf59414
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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