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Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(methylsulfonyl)piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531814
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HRID 531814 반응식
Cl.FC1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCNCC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[F:46][C:47]1[CH:48]=[C:49]([CH:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([S:77]([CH3:80])(=[O:79])=[O:78])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[N:58](S(C3C=CC(C)=CC=3)(=O)=O)[CH:57]=2)[CH:53]=[N:52]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:47]1[CH:48]=[C:49]([CH:91]=[CH:92][CH:93]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([S:77]([CH3:80])(=[O:79])=[O:78])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[NH:58][CH:57]=2)[CH:53]=[N:52]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 900305243-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(methylsulfonyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

생성물 1

HCID 900309503-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(methylsulfonyl)piperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine
수율 35%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-(methylsulfonyl)piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.145 mmol) was hydrolyzed with lithium hydroxide (30 mg, 0.729 mmol) in THF/methanol/water (3/2/1 mL) to yield 27 mg (35.0% yield) of the titled compound after purification by preparative HPLC. 1H NMR (CD3OD, 300 MHz): δ 8.55 (s, 2H), 8.47-8.43 (dd, 1H), 8.386-8.380 (d, 1H), 8.247 (s, 1H), 7.997-7.995 (d, 1H), 7.75 (s, 1H), 7.50-7.47 (d, 1H), 7.37-7.35 (d, 1H), 7.42-7.32 (m, 1H), 7.12-6.97 (m, 3H), 5.43 (s, 2H), 3.88-3.85 (t, 4H), 3.47-3.44 (t, 4H), 2.92 (s, 3H). MS: m/z=532.05 (M+1), HPLC: 95.94% in method A.

후처리

  1. customreaction conditions

출처 및 근거

ORD 기록
ord-904398cfcd7f4d68af42b0186ec2934e
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353107B2

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