1,2-Dichloroethane → N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxamide

HRID 1476479노트

반응식

HRID 1476479 반응식
[CH3:1][CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([S:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)(=[O:15])=[O:14])[CH:9]=[C:8]([C:22]([OH:24])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:25][CH2:26][C:27]1[C:28](=[O:35])[NH:29][C:30]([CH3:34])=[CH:31][C:32]=1[CH3:33].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>O.CS(C)=O>[CH3:33][C:32]1[CH:31]=[C:30]([CH3:34])[NH:29][C:28](=[O:35])[C:27]=1[CH2:26][NH:25][C:22]([C:8]1[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:12]=2[CH:11]=[C:10]([S:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)(=[O:15])=[O:14])[CH:9]=1)=[O:24]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 674681771-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxylic acid

생성물 1

HCID 54596560N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxylic acid (90 mg, 0.255 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (62.5 mg, 0.331 mmol), 1-hydroxy-7-azabenzotriazole (69.3 mg, 0.509 mmol), EDC (98 mg, 0.509 mmol) and N-methylmorpholine (0.112 mL, 1.019 mmol) were added to Dimethyl Sulfoxide (DMSO) (10 mL) and stirred at room temperature for 16 hours. Next added 40 mL of water and stirred for 10 minutes. The contents were extracted with DCM (5×30 mL), washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified via chromatography (eluent: 0% to 100% gradient Hex:EtOAc then 0 to 10% MeOH:EtOAc). The product was collected as 110 mg (88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 2.89-3.05 (m, 4H), 3.54-3.71 (m, 4H), 4.38 (d, J=4.80 Hz, 2H), 5.27 (dt, J=13.07, 6.47 Hz, 1H), 5.90 (s, 1H), 7.80 (d, J=1.01 Hz, 1H), 8.29 (s, 1H), 8.52 (s, 1H), 8.88 (t, J=5.05 Hz, 1H), 11.56 (br. s., 1H); LCMS (ES) [M+H]+ 488.3

후처리

  1. stirringstirred for 10 minutes
  2. extractionThe contents were extracted with DCM (5×30 mL)
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via chromatography (eluent
  8. customThe product was collected as 110 mg (88%)

출처 및 근거

ORD 기록
ord-4d46cf37458245509afcee1c34cf469a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018382B2

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