Pyridine → 2-[(S)-1-Phenylethylamino]-4-[5-(pyridin-2-yl)-benzimidazol-1-yl]pyrimidine

HRID 2300846노트

반응식

HRID 2300846 반응식
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23](N)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=O.[Na+].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([Cu])#N>C(O)(=O)C.O.C(OCC)(=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 98839772-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 98006882-[(S)-1-Phenylethylamino]-4-[5-(pyridin-2-yl)-benzimidazol-1-yl]pyrimidine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 37 mg of 2-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine (EXAMPLE 79) in acetic acid (1.0 mL) was added NaNO2 (7.7 mg) in H2O (0.5 mL). The mixture was stirred 1 h at 0° C. Pyridine (1 mL) was added followed by CuCN (9.8 mg). Gas evolution was observed. The reaction mixture was poured into ethyl acetate and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated. The product mixture was purified by silica gel chromatography eluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound. Mass spectrum (ESI): 293.3 (M+1).

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product mixture was purified by silica gel chromatography
  6. washeluting with a gradient solvent system of 100% CH2Cl2 going to 10% MeOH CH2Cl2 giving 18.3 mg of the title compound

출처 및 근거

ORD 기록
ord-b7826af564db407181a16c8a6cc47c9a
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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