Tetrahydrofuran → 6,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-ylmethoxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61720

반응식

HRID 61720 반응식
Cl.[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:22][C:4]1=2.[O:32]1[CH2:35][C:34](=O)[CH2:33]1.C1COCC1.C([BH3-])#N.[Na+]>C(O)(=O)C.O.CO>[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([CH:34]4[CH2:35][O:32][CH2:33]4)[CH2:27][CH2:26]3)=[CH:22][C:4]1=2

참가 물질

8

실험 절차

6,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt (Compound A7-25, 30 mg, 0.075 mmol) and oxetan-3-one (38 mg, 7 eq.) were dissolved in acetic acid (0.2 ml), THF (1 ml) and methanol (1 ml), added with sodium cyanoborohydride (33 mg, 7 eq.) at room temperature, and stirred overnight. The reaction solution was added with water, and then extracted with ethyl acetate. The solution was dried over sodium sulfate and the solvent was removed under vacuum and the resulting residues were purified by preparative TLC (chloroform: 2 N ammonia methanol=9:1) to obtain the target compound (15 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe solution was dried over sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customthe resulting residues were purified by preparative TLC (chloroform: 2 N ammonia methanol=9:1)

출처 및 근거

ORD 기록
ord-b18223b5a281405fb046a292826eac0a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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