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Lithium Hydroxide → 4-(5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089028
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HRID 2089028 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[CH:25]=[N:26][N:27](S(C5C=CC=CC=5)(=O)=O)[CH:28]=4)[CH:22]=3)[N:17](S(C3C=CC=CC=3)(=O)=O)[CH:16]=2)[CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.O.C(OCC)(=O)C>[NH:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[C:23]3[C:15]([C:4]4[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([NH:8][CH:9]5[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]5)[CH:5]=4)=[CH:16][NH:17][C:18]3=[N:19][CH:20]=2)[CH:28]=[N:27]1
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참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 87192311HCID 87192311, 화합물

생성물 1

HCID 871912104-(5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine수율 23.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매
HCID 21899815
MeOH tetrahydrofuran
용매

실험 절차

A solution of Example 171b (0.110 g, 0.16 mmol) in 18 mL tetrahydrofuran/methanol (2:1) was treated with 1N lithium hydroxide (0.048 g, 2.00 mmol) in 2 mL water at room temperature for 4 hours. The material was diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by trituration with diethyl ether/ethyl acetate and filtration to afford 15 mg of the title compound. 1H NMR (400 MHz, DMSO-d6) ppm 1.17-1.44 (m, 5H) 1.56-1.66 (m, 1H) 1.69-1.80 (m, 2H) 1.92-2.01 (m, 2H) 3.66-3.78 (m, 1H) 6.39 (d, J=7.63 Hz, 1H) 6.83 (d, J=6.71 Hz, 2H) 7.95 (s, 1H) 7.95-8.16 (m, 2H) 8.33 (s, 1H) 8.52 (s, 1H) 11.79 (s, 1H) 12.73 (s, 1H). MS (ESI+) m/z 393.7 (M+H)+.

후처리

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe residue was purified by trituration with diethyl ether/ethyl acetate and filtration

출처 및 근거

ORD 기록
ord-972b19f7ccbb47e998dbe5246c6e18f4
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08435980B2

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