Potassium Carbonate → HCID 118131120, compound

HRID 634438Notes

Reaction equation

HRID 634438 reaction equation
Br[CH:2]([C:4]1[O:5][C:6](=[O:29])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[N:30]1[C:38]([NH2:39])=[C:37]2[C:33]([NH:34][CH:35]=[N:36]2)=[N:32][CH:31]=1.C([O-])([O-])=O.[K+].[K+]>>[NH2:39][C:38]1[N:30]=[CH:31][N:32]=[C:33]2[C:37]=1[N:36]=[CH:35][N:34]2[CH:2]([C:4]1[O:5][C:6](=[O:29])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 118131033HCID 118131033, compound2×HCID 178508693HCID 178508693, compound

Product 1

HCID 118131120HCID 118131120, compoundYield 39.7%

Procedure

The title compound was made in a similar way as that of the compound of example 1, using 3-(1-bromoethyl)-4-(3-(morpholinosulfonyl)phenyl)-1H-isochromen-1-one (intermediate C9, 68 mg, 0.142 mmol), 9H-purin-6-amine (57.6 mg, 0.426 mmol) and K2CO3 (29.5 mg, 0.213 mmol) to give the title compound (30 mg, 37.1%). 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%) The resulting product was further purified by Preparative HPLC (method 2) to give the chemically pure compound (10 mg, 13%) and a batch with lower purity (9 mg, 12%).

Sources & evidence

ORD record
ord-7a6420805027485fb49ad264c98b0940
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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