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Hydrogen Peroxide → 4-amino-6-(((1S)-1-(6-fluoro-1-(3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide

HRID 2036676
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HRID 2036676 반응식
C(=O)([O-])[O-:2].[K+].[K+].[NH2:7][C:8]1[C:13]([C:14]#[N:15])=[C:12]([NH:16][C@H:17]([C:19]2[N:23]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:22]3[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=3[N:20]=2)[CH3:18])[N:11]=[CH:10][N:9]=1.OO>CS(C)=O>[NH2:7][C:8]1[C:13]([C:14]([NH2:15])=[O:2])=[C:12]([NH:16][C@H:17]([C:19]2[N:23]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[C:22]3[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=3[N:20]=2)[CH3:18])[N:11]=[CH:10][N:9]=1
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5

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HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58459229(S)-4-Amino-6-((1-(6-fluoro-1-(pyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)amino)pyrimidine-5-carbonitrile

생성물 1

HCID 584593894-amino-6-(((1S)-1-(6-fluoro-1-(3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide
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온도
0 °C

실험 절차

To an ice-cooled solution of potassium carbonate (0.027 g, 0.19 mmol) and (S)-4-amino-6-(1-(6-fluoro-1-(pyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethylamino)pyrimidine-5-carbonitrile (0.060 g, 0.16 mmol) in DMSO (1.60 mL) was added hydrogen peroxide (31.3% in water, 0.078 mL, 0.80 mmol) dropwise under nitrogen atmosphere. The solution was stirred at 0° C. for 1 h then was partitioned between water and EtOAc. Organic extracts were concentrated under reduced pressure then purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford 4-amino-6-(((1S)-1-(6-fluoro-1-(3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide as an off-white foam. 1H NMR (400 MHz, DMSO-d6) d ppm 1.48 (d, J=6.85 Hz, 3H) 5.26 (quin, J=6.94 Hz, 1H) 6.57 (s, 2H) 6.98 (dd, J=8.90, 2.45 Hz, 1H) 7.14 (ddd, J=9.78, 8.80, 2.54 Hz, 1H) 7.46 (s, 2H) 7.65-7.70 (m, 1H) 7.74 (dd, J=8.80, 4.89 Hz, 1H) 7.77 (s, 1H) 7.94 (d, J=7.63 Hz, 1H) 8.05-8.12 (m, 1H) 8.78 (dd, J=4.79, 1.47 Hz, 1H) 8.82 (d, J=2.15 Hz, 1H). LC-MS (ESI) m/z 393.2 [M+H]+.

후처리

  1. customthen was partitioned between water and EtOAc
  2. concentrationOrganic extracts were concentrated under reduced pressure
  3. customthen purified by MPLC (
  4. washeluted with a gradient of 0-10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-d3ccaf2ef21949eeafd8b8b3e4d447be
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575183B2

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