Potassium Carbonate → HCID 59262782, compound

HRID 908346Notes

Reaction equation

C([Si](C)(C)[O:6][C:7]1[C:8](=O)[C:9](=[CH:13]N(C)C)[CH2:10][CH2:11][CH:12]=1)(C)(C)C.[NH:20]([C:24]1[CH:25]=[C:26]([S:30]([NH2:33])(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)[C:21]([NH2:23])=[NH:22].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[OH:6][C:7]1[C:8]2[N:23]=[C:21]([NH:20][C:24]3[CH:25]=[C:26]([S:30]([NH2:33])(=[O:31])=[O:32])[CH:27]=[CH:28][CH:29]=3)[N:22]=[CH:13][C:9]=2[CH2:10][CH2:11][CH:12]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The crude 2-(tert-butyl-dimethyl-silanyloxy)-6-dimethylaminomethylene-cyclohex-2-enone in DMA (75 mL) was treated with 3-guanidino-benzenesulfonamide as the hydrochloride salt (7.79 g, 31.09 mmol) and potassium carbonate (2.13 g, 15.54 mmol) and the mixture stirred at 110° C. for 20 hours. The mixture was evaporated under high vacuum and triturated with dichloromethane (100 mL) to give a buff coloured precipitate. The precipitate was filtered, the mother liquors concentrated in vacuo and purified by flash chromatography on silica gel eluting with ethyl acetate to give 3-(8-hydroxy-5,6-dihydro-quinazolin-2-ylamino)benzenesulfonamide as a yellow solid (0.63 g, 6.5%). MS (ES+) 319, (ES−) 317. δH (d6 DMSO) 2.04-2.12 (2H, m), 2.66-2.74 (2H, m), 2.84-2.90 (2H, m), 7.33 (2H, s), 7.43 (1H, d), 7.48 (1H, t), 8.16 (1H, d), 8.25 (1H, s), 8.78 (1H, s), 10.25 (1H, s).

Workup

customThe mixture was evaporated under high vacuum
customtriturated with dichloromethane (100 mL)
customto give a buff
filtrationThe precipitate was filtered
concentrationthe mother liquors concentrated in vacuo
custompurified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record: ord-3b18075496a644e0bd0d7d68ef2f0892
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017619B2

Reaction notes

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