(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole → (S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine

HRID 928217ノート

反応式

HRID 928217 の反応式
[CH3:1][O:2][C:3]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]([C@H:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[N:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[C:7]([NH2:8])=[CH:6][N:5]([C@H:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[N:4]=1

参加物

4

反応物 1

HCID 118073571(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole

生成物 1

HCID 118073561(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A nitrogen-flushed round bottom flask was charged with (S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole (300 mg, 1.33 mmol, 1.00 eq), 10% Pd/C (200 mg) and methanol (20 mL). The reaction mixture was sparged with hydrogen for 10 min then stirred vigorously under hydrogen atmosphere for 16 hr. The reaction mixture was then sparged with nitrogen, filtered through Celite®, and concentrated to give an oil that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.99 (s, 1H), 4.51 (tdd, J=4.8, 7.3, 9.3 Hz, 1H), 3.74 (s, 3H), 3.36 (br. s., 2H), 2.71-2.61 (m, 2H), 2.57 (dd, J=4.8, 9.5 Hz, 1H), 2.40 (dt, J=6.5, 8.3 Hz, 1H), 2.25 (s, 3H), 2.23-2.14 (m, 1H), 1.94-1.84 (m, 1H). m/z (APCI+) for C9H17N4O 197.3 (M+H)+.

後処理

  1. customA nitrogen-flushed round bottom flask
  2. customThe reaction mixture was sparged with hydrogen for 10 min
  3. customThe reaction mixture was then sparged with nitrogen
  4. filtrationfiltered through Celite®
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas used without further purification

出典と根拠

ORDレコード
ord-ee02079405684b9db75e9af6b100d351
出典データセット
uspto-grants-2016_03
特許番号
US09290496B2

反応ノート

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