HCID 68519649、化合物 → HCID 68515091、化合物

HRID 1171025ノート

反応式

HRID 1171025 の反応式
[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

参加物

4

反応物 1

HCID 68519649HCID 68519649、化合物

生成物 1

HCID 68515091HCID 68515091、化合物収率 93%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-8a41d6d246c34ebb995b648fdd9b4bd1
出典データセット
uspto-grants-2010_11
特許番号
US07829570B2

反応ノート

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