1,2-Dichloroethane → HCID 56597707、化合物

HRID 475970

反応式

HRID 475970 の反応式
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([OH:18])=O)[C:7]3[CH:12]=[N:11][N:10]([CH:13]([CH3:15])[CH3:14])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.ON1C2N=CC=CC=2N=N1.[NH2:29][CH2:30][C:31]1[C:32](=[O:42])[NH:33][C:34]([CH3:41])=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38].CN1CCOCC1.C(Cl)CCl>CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([NH:29][CH2:30][C:31]3[C:32](=[O:42])[NH:33][C:34]([CH3:41])=[CH:35][C:36]=3[C:37]([F:38])([F:39])[F:40])=[O:18])[C:7]3[CH:12]=[N:11][N:10]([CH:13]([CH3:14])[CH3:15])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 25259926-cyclopropyl-1-(propan-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 671240553-(Aminomethyl)-6-methyl-4-(trifluoromethyl)-2(1h)-pyridinone

生成物 1

HCID 56597707HCID 56597707、化合物

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

The title compound was prepared in the same manner as described in example 19 from 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.12 g, 0.489 mmol), 1-hydroxy-7-azabenzotriazole (0.100 g, 0.734 mmol), 3-(aminomethyl)-6-methyl-4-(trifluoromethyl)-2(1H)-pyridinone (0.154 g, 0.636 mmol, DMSO (3.0 mL), N-methylmorpholine (0.215 mL, 1.957 mmol), and EDC (0.141 g, 0.734 mmol) The crude solid was purified by silica gel chromatography (eluent: gradient 5-100% of 10% 2M NH3 (in MeOH/DCM) and DCM) and the collected product dried in vacuum oven for 5 h. The final product was collected as 0.112 g (50%). LCMS E-S (M+H)=434.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.12 (m, 4H), 1.47 (d, J=6.82 Hz, 6H), 2.20-2.33 (m, 4H), 4.34-4.54 (m, 2H), 5.12 (quin, J=6.63 Hz, 1H), 6.33 (s, 1H), 7.39 (s, 1H), 8.18 (s, 1H), 8.70 (t, J=4.04 Hz, 1H), 12.43 (s, 1H).

後処理

  1. customwas purified by silica gel chromatography (eluent: gradient 5-100% of 10% 2M NH3 (in MeOH/DCM) and DCM)
  2. customthe collected product dried in vacuum oven for 5 h
  3. customThe final product was collected as 0.112 g (50%)

出典と根拠

ORDレコード
ord-383de30673504d5cb1b7a5dcd40200bc
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

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