HCID 68519649, 화합물 → HCID 68515091, 화합물

HRID 1171025노트

반응식

HRID 1171025 반응식
[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH3:21])[CH:12]=3)[N:9]=[C:8]([C:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH:27]=3)[C:4]=2[N:5]=[CH:6][N:7]=1>[Pd].CO>[NH2:1][C:2]1[C:3]2[N:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH3:21])[CH:12]=3)[N:9]=[C:8]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

4

반응물 1

HCID 68519649HCID 68519649, 화합물

생성물 1

HCID 68515091HCID 68515091, 화합물수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of tert-butyl 4-[7-amino-1-(3-methoxy-4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate (200 mg, 0.428 mmol) and 10% palladium on carbon (100 mg) in methanol (20 mL) and hydrogenated in a Parr shaker at 55 psi for 18 hours. The catalyst was removed by filtration through a pad of diatomaceous earth and the filtrate concentrated under reduced pressure then the residue was dissolved methanol (20 mL). Platinum (IV) oxide (100 mg) was added and the mixture was hydrogenated in a Parr shaker at 55 psi for 30 hours. The catalyst was removed by filtration through a pad of diatomaceous earth and the filtrate concentrated under reduced pressure to provide the title compound as a brown solid (175 mg, 93%): 1H NMR (DMSO-d6, 400 MHz) δ 8.22 (s, 1H), 6.96 (d, 1H), 6.84 (d, 1H), 6.74 (d, 1H), 6.5 (bs, 2H), 5.75 (bs, 2H), 4.03 (m, 2H), 3.76 (s, 3H), 3.22 (m, 1H), 2.93 (m, 2H), 1.7-2.1 (m, 4H), 1.42 (s, 9H) RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 16.93 min; MS: MH+ 440.2

후처리

  1. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionthe residue was dissolved methanol (20 mL)
  4. additionPlatinum (IV) oxide (100 mg) was added
  5. waitthe mixture was hydrogenated in a Parr shaker at 55 psi for 30 hours
  6. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  7. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8a41d6d246c34ebb995b648fdd9b4bd1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829570B2

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