Triethylamine → N-(2-fluoropyridin-4-yl)-5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

HRID 1776438노트

반응식

HRID 1776438 반응식
[CH3:1][O:2][C:3]1[C:4]([NH2:27])=[N:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:10]=2)=[N:7][CH:8]=1.[F:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[CH:31][N:30]=1.C(N(CC)CC)C>ClC(Cl)Cl.CN(C)C1C=CN=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:28][C:29]1[CH:34]=[C:33]([NH:27][C:4]2[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[N:10]=3)[N:5]=2)[CH:32]=[CH:31][N:30]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 27833962-Fluoropyridine-4-boronic acidHCID 867324165-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

생성물 1

HCID 86732467N-(2-fluoropyridin-4-yl)-5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 6212Chloroform용매

실험 절차

100 mg of 5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine (1-4-1, 0.277 mmol, 1. eq.), 78.0 mg of (2-fluoropyridin-4-yl)boronic acid (0.553 mmol, 2 eq.) and 205 mg of copper (II) acetate were suspended in 4 ml of trichloromethane. 154 μl of triethylamine (1.11 mmol, 4 eq.) and 16.9 mg of N,N-dimethylpyridin-4-amine (138 mmol, 0.5 eq.) were added. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered off over Celite 545 and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography and preparative HPLC to yield 13 mg (0.03 mmol, 10.9%) of the analytically pure target compound.

후처리

  1. filtrationThe reaction mixture was filtered off over Celite 545
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography and preparative HPLC
  5. customto yield 13 mg (0.03 mmol, 10.9%) of the analytically pure target compound

출처 및 근거

ORD 기록
ord-19348cd8f8cc4dc59654aec4049b2421
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265763B2

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