4-Methylmorpholine → 6-chloro-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

HRID 1476377노트

반응식

HRID 1476377 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[NH2:17][CH2:18][C:19]1[C:20](=[O:29])[NH:21][C:22]([CH3:28])=[CH:23][C:24]=1[CH2:25][CH2:26][CH3:27].ON1C2N=CC=CC=2N=N1.CN1CCOCC1>C(Cl)CCl.CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:17][CH2:18][C:19]2[C:20](=[O:29])[NH:21][C:22]([CH3:28])=[CH:23][C:24]=2[CH2:25][CH2:26][CH3:27])=[O:16])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 181649HOAt2회HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674688776-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

생성물 1

HCID 545964886-chloro-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 679Dimethyl Sulfoxide용매

실험 절차

6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (0.10 g, 0.419 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (0.109 g, 0.503 mmol), 1-hydroxy-7-azabenzotriazole (0.080 g, 0.587 mmol), and then EDC (0.112 g, 0.587 mmol) were added to DMSO (4.0 mL). N-methylmorpholine (0.184 mL, 1.676 mmol) was quickly added via syringe. The contents were stirred at RT overnight Additional HOAT and EDC were added, and the contents were stirred for another 6 h. The contents were slowly poured onto 45 mL of ice-water wherein solid precipitation occurred. The contents were stirred for 10 min., and then allowed to stand for another 10 min. The contents were filtered, the collected solid washed with ca. 5 mL of water. The solid was air dried for 15 min. then dried in vacuum oven at 45° C. for 24 h. The title compound was collected as a white solid (0.160 g, 93% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=7.33 Hz, 3H) 1.42-1.58 (m, 8H) 2.14 (s, 3H) 2.52-2.58 (m, 1H) 4.36 (d, J=5.05 Hz, 2H) 5.04 (quin, J=6.57 Hz, 1H) 5.91 (s, 1H) 7.59 (d, J=1.52 Hz, 1H) 8.06 (s, 1H) 8.38 (s, 1H) 8.61 (t, J=4.80 Hz, 1H) 11.54 (s, 1H); MS (ES) [M+H]+ 400.9.

후처리

  1. additionwere added
  2. stirringThe contents were stirred for 10 min.
  3. waitto stand for another 10 min
  4. filtrationThe contents were filtered
  5. washthe collected solid washed with ca. 5 mL of water
  6. customdried for 15 min.
  7. customthen dried in vacuum oven at 45° C. for 24 h

출처 및 근거

ORD 기록
ord-fd2ef06c2e594053804ae350c2d44414
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018382B2

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