Methanol → HCID 58763666, 화합물

HRID 2110176노트

반응식

HRID 2110176 반응식
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:5].CO.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][N:25]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[Br:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][NH:1][C:2]2[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=2[C:4]([NH:6][C:7]2[N:8]=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:5])=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 601321962-Amino-N-(isoquinolin-3-yl)benzamide

생성물 1

HCID 58763666HCID 58763666, 화합물수율 57.3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

3.46 g (13.17 mmol) of 2-amino-N-isoquinolin-3-yl-benzamide is introduced into 50 ml of methanol, mixed with 1.5 ml of glacial acetic acid as well as 2.45 g (13.17 mmol) of 2-bromopyridine-5-carbaldehyde and stirred for 24 hours under argon and in a moisture-free environment at room temperature. Then, it is mixed with 828 mg (13.17 mmol) of sodium cyanoborohydride and stirred for another 24 hours at room temperature. After concentration by evaporation under vacuum, the residue is taken up in dilute sodium bicarbonate solution and suctioned off. The residue that is obtained is absorptively precipitated in a little ethyl acetate and suctioned off repeatedly. The residue that is obtained in this case is chromatographed on silica gel with hexane:ethyl acetate=1:1 as an eluant. 3.27 g (57% of theory) of 2-[(6-bromo-pyridin-3-ylmethyl)-amino]-N-isoquinolin-3-yl-benzamide is obtained.

후처리

  1. stirringstirred for another 24 hours at room temperature
  2. concentrationAfter concentration
  3. customby evaporation under vacuum
  4. customThe residue that is obtained
  5. customis absorptively precipitated in a little ethyl acetate
  6. customThe residue that is obtained in this case
  7. customis chromatographed on silica gel with hexane

출처 및 근거

ORD 기록
ord-e65fa540b54e40b79ea9333191492a7f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517894B2

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