2-Pyrrolidone → HCID 57799574, compound

HRID 2101132Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:16][C:17]3[CH:21]=[C:20]([CH3:22])[N:19](S(C(F)(F)F)(=O)=O)[N:18]=3)[N:8]=[C:9]2[O:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1OS(C(F)(F)F)(=O)=O.[NH:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:16][C:17]3[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=3)[N:8]=[C:9]2[O:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:38]1[CH2:42][CH2:41][CH2:40][C:39]1=[O:43]

Participants

Conditions

Temperature: 100 °C

Procedure

Under Ar, trifluoro-methanesulfonic acid 7-fluoro-1-isopropoxy-3-(5-methyl-1-trifluoromethanesulfonyl-1H-pyrazol-3-ylamino)-isoquinolin-6-yl ester (60 mg), pyrrolidin-2-one, Pd2 (dba)3 (4.8 mg), Xantphos (12 mg) and K3PO4 (61.8 mg) were added to dioxane (5 ml), the mixture was heated at 100° C. for 20 hrs. The mixture was filtrated, and the filtrate was concentrated to give crude product. It was purified by preparative LC-MS to give 1-[7-Fluoro-1-isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-yl]-pyrrolidin-2-one (20 mg). LC-MS: m/e 384 (MH+).

Workup

filtrationThe mixture was filtrated
concentrationthe filtrate was concentrated
customto give crude product
customIt was purified by preparative LC-MS

Sources & evidence

ORD record: ord-0b714f2aa99542dc8be4edd24384eab0
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Reaction notes

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