Sodium hydride → HCID 178509490, 화합물

HRID 1398490노트

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HRID 1398490 반응식
Cl[CH:2]1[NH:7][C:6]([NH2:8])=[N:5][CH:4]=[C:3]1[N+:9]([O-:11])=[O:10].[H-].[Na+].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=2)[CH:16]=[N:15]1>CN(C=O)C>[NH2:8][C:6]1[NH:7][CH:2]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[CH:16]=[N:15]2)[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][N:5]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 4225291H-indazole-6-carbonitrileHCID 178508523HCID 178508523, 화합물

생성물 1

HCID 178509490HCID 178509490, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-chloro-5-nitro-1,6-dihydropyrimidin-2-amine (538.5 mg, 60% purity, 2.00 mmol) in DMF (10 mL) was added NaH (60% oil suspension, 172 mg, 4.30 mmol) at 0° C. Mixture was stirred at RT for 10 min before addition of 1H-indazole-6-carbonitrile (410 mg, 2.87 mmol). Stirring was continued at RT for 18 hr. The reaction mixture was quenched with water (25 mL) cooled in an ice bath and extracted with EtOAc (3×20 mL). Insoluble solid formed during extraction was separated out. Combined EtOAc extract was washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. A portion (70 mg) of the crude product was purified by reverse phase preparative HPLC to give the title compound: 1H NMR (250 MHz, DMSO) δ 7.79 (1 H, dd, J=8.22, 1.07 Hz), 8.14 (1H, d, J=8.22 Hz), 8.20 (1H, br. s.), 8.33 (1H, br. s.), 8.65 (1H, s), 8.91 (1H, s), 9.03 (1H, s); LC-MS: m/z=+281.95 (M+H)+.

후처리

  1. customThe reaction mixture was quenched with water (25 mL)
  2. temperaturecooled in an ice bath
  3. extractionextracted with EtOAc (3×20 mL)
  4. customInsoluble solid formed during extraction
  5. customwas separated out
  6. extractionCombined EtOAc extract
  7. washwas washed with water (20 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customA portion (70 mg) of the crude product was purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-95557195f6cf49499890de38052fe0aa
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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