Diisopropylethylamine → US9433622, Dmx-131

HRID 55867

반응식

HRID 55867 반응식
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]

참가 물질

6

반응물 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

생성물 1

HCID 90369534US9433622, Dmx-131

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3168bd04921344eab3ba7adbb865797e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433622B2

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