Cesium carbonate → HCID 67051304, compound

HRID 1025038Notes

Reaction equation

[N:1]1([S:5]([NH2:8])(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH:9]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)[CH2:14]CCC[CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:50]1[N:55]=[C:54]([S:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([F:64])[C:59]=2[F:65])[N:53]=[C:52]([C@@H]2CCC[C@H]2O)[CH:51]=1.[O:72]1[CH2:77][CH2:76][O:75]CC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:65][C:59]1[C:60]([F:64])=[CH:61][CH:62]=[CH:63][C:58]=1[CH2:57][S:56][C:54]1[N:55]=[C:50]([NH:8][S:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:7])=[O:6])[CH:51]=[C:52]([O:72][C@@H:77]2[CH2:14][CH2:9][CH2:10][C@H:76]2[OH:75])[N:53]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of azetidine-1-sulfonamide (0.27 g), tris(dibenzylideneacetone)dipalladium (0) (50 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (50 mg), cesium carbonate (0.43 g) and (trans)-2-{6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}cyclopentanol (the product from step i), 0.50 g) in dioxane (20 ml) was heated at reflux in a microwave at 100° C., 300 W, open vessel with cooling for 1 h. The reaction mixture was then reduced in vacuo and the residue partitioned between DCM (150 ml) and H2O (150 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced under vacuo and the resulting residue purified by prep HPLC to give the title compound as a white solid. Yield 74 mg

Workup

temperaturewas heated
temperature300 W, open vessel with cooling for 1 h
customthe residue partitioned between DCM (150 ml) and H2O (150 ml)
customThe organics were separated
extractionthe aqueous layer was re-extracted with DCM (2×150 ml)
dry with materialdried (MgSO4)
customthe resulting residue purified by prep HPLC

Sources & evidence

ORD record: ord-46e558727ddb4cdf92fe218cc9626c61
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722883B2

Reaction notes

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