1,2-Dichloroethane → N-[(4-Cyclohexyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522354노트

반응식

HRID 1522354 반응식
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].FC(F)(F)C(O)=O.[NH2:29][CH2:30][C:31]1[C:32](=[O:44])[NH:33][C:34]([CH3:43])=[CH:35][C:36]=1[CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[CH:37]1([C:36]2[CH:35]=[C:34]([CH3:43])[NH:33][C:32](=[O:44])[C:31]=2[CH2:30][NH:29][C:13]([C:12]2[C:7]3[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=3[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=2)=[O:15])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 671244353-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone TFA

생성물 1

HCID 56597703N-[(4-Cyclohexyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide수율 47.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (169 mg, 0.6 mmol), 3-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone trifluoroacetate (221 mg, 0.660 mmol), EDC (150 mg, 0.780 mmol), HOAT (106 mg, 0.780 mmol), and N-methylmorpholine (0.264 mL, 2.400 mmol) in DMF(3 mL) were stirred at room temperature for 6 days. water (15 mL) was added to the slurry, and it was stirred for an hour. The precipitate was then collected by vacuum filtration and rinsed with EtOH (4 mL), and the solid was dried in the vacuum oven overnight to give the title compounds as an off-white solid (137 mg, 45%). LCMS E-S (M+H)=485.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.44 (m, 5 H), 1.56 (d, J=6.57 Hz, 6 H), 1.55-1.72 (m, 5 H), 2.15 (s, 3 H), 2.80-2.92 (m, 1 H), 4.53 (d, J=4.55 Hz, 2 H), 5.36 (spt, J=6.53 Hz, 1 H), 6.03 (s, 1 H), 8.18-8.23 (m, 2 H), 8.26 (s, 1 H), 8.45 (s, 1 H), 8.75-8.82 (m, 2 H), 9.01 (t, J=4.55 Hz, 1 H), 11.59 (s, 1 H).

후처리

  1. stirringwas stirred for an hour
  2. filtrationThe precipitate was then collected by vacuum filtration
  3. washrinsed with EtOH (4 mL)
  4. customthe solid was dried in the vacuum oven overnight

출처 및 근거

ORD 기록
ord-8cb76c06c881439995764d46b0222972
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073924B2

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