Diisopropylethylamine → US9433622, Dmx-131

HRID 55867

反応式

HRID 55867 の反応式
Cl[C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[N:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[N:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH:31]1[CH2:35][CH2:34][CH2:33][CH:32]1[CH2:36][C:37]([NH2:39])=[O:38].CCN(C(C)C)C(C)C.CO.C(Cl)(Cl)Cl>CCO>[C:4]([C:3]1[C:2]([N:31]2[CH2:35][CH2:34][CH2:33][CH:32]2[CH2:36][C:37]([NH2:39])=[O:38])=[N:9][CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:18]=[N:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[N:11]=2)[CH:6]=1)#[N:5]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 21584188Chloroform methanolHCID 695393622-(Pyrrolidin-2-yl)acetamide hydrochlorideHCID 903695292-Chloro-5-[2-(6-morpholin-4-ylmethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-nicotinonitrile

生成物 1

HCID 90369534US9433622, Dmx-131

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of compound 18 (100 mg, 0.24 mmol) in EtOH (5 mL) was added 2-(pyrrolidin-2-yl)acetamide-HCl (160 mg, 1.22 mmol) and DIPEA (0.22 mL, 1.22 mmol) at rt and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to rt, concentrated to half of its volume and triturated with n-pentane, the precipitated solid was collected by filtration to obtain DMX-130 (80 mg, 65%) as a white solid. Rf: 0.4 (10% MeOH/CHCl3); (m/z): 499.8 [M+1]+; 1H NMR (300 MHz, DMSO-d6): δ 9.77 (1H, s), 9.13 (1H, d, J=2.4 Hz), 8.87 (1H, d, J=2.4 Hz), 8.66 (1H, d, J=1.8 Hz), 8.50 (1H, d, J=5.1 Hz), 8.16 (1H, dd, J=2.7, 9.0 Hz), 7.46 (1H, d, J=5.7 Hz), 7.38 (1H, d, J=9.0 Hz), 7.30 (1H, br), 6.84 (1H, br), 4.74 (1H, br), 3.97 (1H, br), 3.80-3.76 (1H, br), 3.59-3.53 (6H, m), 2.76-2.70 (1H, m), 2.40 (4H, br), 2.23-2.15 (1H, m), 2.10-2.98 (3H, m), 1.86-1.84 (1H, m).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated to half of its volume
  4. customtriturated with n-pentane
  5. filtrationthe precipitated solid was collected by filtration
  6. customto obtain DMX-130 (80 mg, 65%) as a white solid

出典と根拠

ORDレコード
ord-3168bd04921344eab3ba7adbb865797e
出典データセット
uspto-grants-2016_09
特許番号
US09433622B2

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