Potassium Carbonate → HCID 178448741, 화합물

HRID 30973

반응식

HRID 30973 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 178448739HCID 178448739, 화합물

생성물 1

HCID 178448741HCID 178448741, 화합물수율 49.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d8afea77e3c245abb45d6f1465c7d0da
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425552B2

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