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 85513ノート

反応式

HRID 85513 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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

後処理

  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%)

出典と根拠

ORDレコード
ord-db4b5a44885f437890376fb3be7c35fa
出典データセット
uspto-grants-2014_09
特許番号
US08846935B2

反応ノート

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