Potassium Hydroxide → 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 2234686노트

반응식

HRID 2234686 반응식
[F:1][C:2]1[C:3]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[OH-].[K+]>O1CCCC1.CO>[F:1][C:2]1[C:3]([NH:40][CH2:41][C:42]2[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=2)=[C:4]([CH:10]=[C:11]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 577315803-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

생성물 1

HCID 577314363-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

3-Fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide was dissolved in a mixture of tetrahydrofuran and methanol. A solution of aqueous potassium hydroxide (50% w/v) was added to the reaction mixture, and the combined mixture was allowed to stir for 1 hour at room temperature. The reaction mixture was quenched with sodium bicarbonate solution, and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes) to afford 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-2-[(pyridin-4-ylmethyl)-amino]-benzamide. 1H-NMR (250 MHz, DMSO-d6) δ 11.87 (s, 1H), 8.53-8.41 (m, 3H), 8.09 (d, J=2.0 Hz, 1H), 7.70 (d, J=2.6 Hz, 1H), 7.60 (dd, J=7.5, 1.5 Hz, 1H), 7.52 (dd, J=14.0, 2.0 Hz, 1H), 7.33-7.21 (m, 3H), 7.17 (d, J=1.6 Hz, 1H), 7.11 (d, J=7.9 Hz, 1H), 7.04 (t, J=7.4 Hz, 1H), 6.01 (broad s, 1H), 4.42 (d, J=6.6 Hz, 2H), 3.80 (s, 3H), 2.89 (s, 12H), 2.59 (s, 12H); MS: m/z 496.3 (M+H+).

후처리

  1. customThe reaction mixture was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (0-100% [10% methanol in ethyl acetate] in hexanes)

출처 및 근거

ORD 기록
ord-7abbb4d9a36e4a71b4e98c175e2c8d60
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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