1,2-Dichloroethane → HCID 68078786、化合物

HRID 475966

反応式

HRID 475966 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.Cl.[NH2:20][CH2:21][C:22]1[C:23](=[O:32])[NH:24][C:25]([CH:29]2[CH2:31][CH2:30]2)=[CH:26][C:27]=1[CH3:28].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>O.CS(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]([NH:20][CH2:21][C:22]3[C:23](=[O:32])[NH:24][C:25]([CH:29]4[CH2:30][CH2:31]4)=[CH:26][C:27]=3[CH3:28])=[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

8

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 67124164HCID 67124164、化合物

生成物 1

HCID 68078786HCID 68078786、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a 4 mL solution of DMSO were sequentially added 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.11 g, 0.448 mmol), 3-(aminomethyl)-6-cyclopropyl-4-methyl-2(1H)-pyridinone hydrochloride (0.106 g, 0.493 mmol), 1-hydroxy-7-azabenzotriazole (0.073 g, 0.538 mmol), EDC (0.103 g, 0.538 mmol), and then N-methylmorpholine (0.197 mL, 1.79 mmol) via syringe. After stirring overnight at room temperature, the suspension was diluted with 50 mL of water and stirred for 15 min. After standing at room temperature for 15 min., the reaction mixture was filtered and the collected solid washed with additional water. The solid was then dried in a vacuum oven at 45° C. for 4 h. The product was obtained as 0.165 g (89%). LCMS E-S (M+H)=406.5. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.76-0.82 (m, 2H), 0.91-0.98 (m, 2H), 1.03-1.12 (m, 4H), 1.46 (d, J=6.82 Hz, 6H), 1.74-1.84 (m, 1H), 2.19 (s, 3H), 2.21-2.31 (m, 1H), 4.34 (d, J=5.05 Hz, 2H), 5.05-5.18 (m, 1H), 5.73 (s, 1H), 7.42 (s, 1H), 8.21 (s, 1H), 8.72 (t, J=4.93 Hz, 1H), 11.61 (br. s., 1H).

後処理

  1. stirringstirred for 15 min
  2. waitAfter standing at room temperature for 15 min.
  3. filtrationthe reaction mixture was filtered
  4. washthe collected solid washed with additional water
  5. customThe solid was then dried in a vacuum oven at 45° C. for 4 h
  6. customThe product was obtained as 0.165 g (89%)

出典と根拠

ORDレコード
ord-da854bcbfe264545ab2f87d6b0d72485
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

関連ノート

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