Potassium Phosphate, Tribasic → HCID 178461687, compound

HRID 717313Notes

Reaction equation

[CH2:1]([C@:8]1([C:24]2[NH:28][C:27]3[CH:29]=[CH:30][C:31](Br)=[CH:32][C:26]=3[N:25]=2)[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[N:42]1[CH2:43][N:44](B(O)O)[CH:45]=[CH:46][CH:47]=1>C(O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH2:1]([C@:8]1([C:24]2[NH:28][C:27]3[CH:29]=[CH:30][C:31]([C:46]4[CH:47]=[N:42][CH:43]=[N:44][CH:45]=4)=[CH:32][C:26]=3[N:25]=2)[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of (5R)-5-benzyl-5-(5-bromo-1H-benzimidazol-2-yl)-3-[(1R)-1-(4-fluorophenyl)ethyl]-1,3-oxazolidine-2,4-dione (25 mg), Pd(OAc)2 (1 mg), dppf (5.5 mg), K3PO4 (31 mg), 3-pyrimidinyl boronic acid (12 mg) in 0.5 mL of ethanol was heated at 120° C. in microwave for 5 min. The reaction mixture was diluted with EtOAc, filtered, concentrated, and then purified via Gilson RP-HPLC (30-100% MeCN/water w/0.1% TFA) to give the title compound. LC/MS 508.1 (M+1). IC50 value=A rating

Workup

filtrationfiltered
concentrationconcentrated
custompurified via Gilson RP-HPLC (30-100% MeCN/water w/0.1% TFA)

Sources & evidence

ORD record: ord-bc42f9b2719d468db6deaaf772401301
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193717B2

Reaction notes

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