Potassium Carbonate → HCID 178477343, compound

HRID 634443Notes

Reaction equation

[N:1]1[C:9]([S:10]CC2OC(=O)C3C(C=2C2C=CC=CC=2)=CC=CC=3)=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.Br[CH:30]([C:32]1[O:33][C:34](=[O:49])[C:35]2[C:40]([C:41]=1[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=1)=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:31].O.N1C(S)=C2C(NC=N2)=NC=1.C([O-])([O-])=O.[K+].[K+]>>[N:1]1[C:9]([S:10][CH:30]([C:32]2[O:33][C:34](=[O:49])[C:35]3[C:40]([C:41]=2[C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=2)=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH3:31])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 1181310803-(1-Bromoethyl)-4-(3-fluorophenyl)-1H-isochromen-1-one2×

HCID 178519204HCID 178519204, compound

HCID 178527205HCID 178527205, compound

Product 1

HCID 178477343HCID 178477343, compoundYield 63%

Procedure

The title compound was made in a similar way as that of the compound of example 10, 3-(1-bromoethyl)-4-(3-fluorophenyl)-1H-isochromen-1-one (intermediate C6, 70 mg, 0.202 mmol), 9H-purine-6-thiol hydrate (34.3 mg, 0.202 mmol) and K2CO3 (27.9 mg, 0.202 mmol). The resulting mixture was straightforward purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound (53 mg, 63%).

Workup

customThe resulting mixture was straightforward purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Sources & evidence

ORD record: ord-9682fd0538ac46d983dbf864d7a8739a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321776B2

Reaction notes

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