Ethanol → HCID 178458593, 화합물

HRID 450401노트

반응식

HRID 450401 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([NH:21][C:22]3[CH:26]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[NH:24][N:23]=3)[N:13]=2)[CH2:9][OH:10])=[N:6][CH:7]=1.[CH2:31](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:11][C:12]2[N:13]=[C:14]3[N:21]([C:22]4[CH:26]=[C:25]([O:27][CH:28]([CH3:30])[CH3:29])[NH:24][N:23]=4)[CH:31]=[N:18][C:15]3=[CH:16][CH:17]=2)[CH2:9][OH:10])=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 178458670HCID 178458670, 화합물2회

생성물 1

HCID 178458593HCID 178458593, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 57417360Sodium chloride; water용매

실험 절차

(2R)-2-(5-fluoropyridin-2-yl)-2-({6-[(5-isopropoxy-1H-pyrazol-3-yl)amino]-5-nitropyridin-2-yl}amino)ethanol (Intermediate 24, 0.45 g) was dissolved into ethanol (20 mL) with Pd—C (90 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 85° C. for 4 hours. Ethyl acetate (40 mL) was added into the resulting mixture, and brine (10 mL×3) was used to wash the organic layer. The organic layer was dried and concentrated. The resulting residue was separated by a silica gel column (Ethyl acetate/MeOH) to afford 0.075 g of the title compound. MS (electrospray): 398 (M+1) for C19H20FN7O2. 1H NMR (300 MHz, CD3OD) δ ppm 8.50 (d, 1H) 8.30 (s, 1H) 7.80 (d, 1H) 7.50 (dd, 1H) 6.70 (d, 1H) 6.05 (s, 1H) 5.20 (m, 1H) 4.65 (m, 1H) 4.00 (m, 2H), 1.55-1.35 (m, 6H).

후처리

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 85° C. for 4 hours
  4. washto wash the organic layer
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe resulting residue was separated by a silica gel column (Ethyl acetate/MeOH)

출처 및 근거

ORD 기록
ord-aefffef5313f4728a8206d8154b15371
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486966B2

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