Potassium Carbonate → HCID 178448741, compound

HRID 30973

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-Butyl-5-hydroxy-4-(7-hydroxy-1,1-dioxo-1,2-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-6-isopropyl-2H-pyridazin-3-one (5f) (38.7 mg, 95.2 μmol) in anhydrous DMF (4 mL), 2-Bromo-acetamide (14.5 mg, 104.7 μmol) was added followed by K2CO3 (39.5 mg, 285.6 μmol). The resulted mixture was heated at 80° C. overnight with stirring. The reaction mixture was concentrated under reduced vacuum and the residue was purified by flash chromatography on silica gel to give the desired product (5g) (21.7 mg) in 49.2% yield. 1H NMR (400 MHz, DMSO-d6): δ7.63-7.66 (m, 1H), 7.62 (br, 1 H), 7.40 (br, 1H), 7.34-7.39 (m, 2 H), 4.58 (s, 2H), 4.10 (m, 2H), 3.23 (m, 1H, J=6.8 Hz), 1.72 (m, 2H, J=7.2 Hz), 1.32 (m, 2H. J=7.2 Hz), 1.21 (d, 6H, J=6.4 Hz), 0.91 (t, 3H, J=7.2 Hz); LC-MS (ESI+): m/e=464.1-[M+1]+ (exact MS: 463.15).

Workup

concentrationThe reaction mixture was concentrated under reduced vacuum
customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-d8afea77e3c245abb45d6f1465c7d0da
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425552B2

Linked notes

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