(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 928217노트

반응식

HRID 928217 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ee02079405684b9db75e9af6b100d351
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290496B2

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