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Ethanol → HCID 178466891, 화합물

HRID 450402
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HRID 450402 반응식
[CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][C@H:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)[CH2:18][OH:19])[CH:13]=[CH:12][C:11]=2[N+:27]([O-])=O)[CH:5]=1)[CH3:2].[CH2:30](O)C.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([N:9]2[C:10]3=[N:15][C:14]([NH:16][C@H:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)[CH2:18][OH:19])=[CH:13][CH:12]=[C:11]3[N:27]=[CH:30]2)[CH:5]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 178466927(2R)-2-({6-[(5-Ethoxy-1H-pyrazol-3-yl)amino]-5-nitropyridin-2-yl}amino)-2-(5-fluoropyridin-2-yl)ethanol2회

생성물 1

HCID 178466891HCID 178466891, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 57417360
Sodium chloride; water
용매

실험 절차

(2R)-2-({6-[(5-ethoxy-1H-pyrazol-3-yl)amino]-5-nitropyridin-2-yl}amino)-2-(5-fluoropyridin-2-yl)ethanol (Intermediate 27, 0.2 g) was dissolved into ethanol (20 mL) with Pd—C (50 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formylamidine 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 silica gel column (Ethyl acetate/MeOH) to afford 0.06 g of the title compound MS (electrospray): 384 (M+1) for C18H18FN7O2. 1H NMR (300 MHz, CD3OD) δ ppm 8.20 (d, 1H) 8.15 (s, 1H) 7.50 (d, 1H) 7.30 (dd, 1H) 6.40 (d, 1H) 5.85 (s, 1H) 5.00 (m, 1H) 4.00 (d, 2H) 3.80 (m, 2H) 1.00 (t, 3H).

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 silica gel column (Ethyl acetate/MeOH)

출처 및 근거

ORD 기록
ord-c639769955764ba98079db4680dc9f6b
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486966B2

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