Ammonium formate → (R)-4-(3-aminopiperidin-1-yl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide

HRID 1811100노트

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HRID 1811100 반응식
[C:1]([C:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:17]([N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[O:18])[CH:13]=3)[C:8]=2[C:7]([N:26]2[CH2:31][CH2:30][CH2:29][C@@H:28]([NH:32]C(=O)OCC3C=CC=CC=3)[CH2:27]2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].C([O-])=O.[NH4+]>[Pd].CO>[NH2:32][C@@H:28]1[CH2:29][CH2:30][CH2:31][N:26]([C:7]2[C:8]3[C:9]4[C:14](=[CH:13][C:12]([C:17]([N:19]5[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]5)=[O:18])=[CH:11][CH:10]=4)[NH:15][C:16]=3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=2)[CH2:27]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 46834656(R)-benzyl 1-(1-carbamoyl-7-(4-methylpiperazine-1-carbonyl)-9H-carbazol-4-yl)piperidin-3-ylcarbamate

생성물 1

HCID 59375032(R)-4-(3-aminopiperidin-1-yl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide수율 122.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
75 °C

실험 절차

A mixture of (R)-benzyl 1-(1-carbamoyl-7-(4-methylpiperazine-1-carbonyl)-9H-carbazol-4-yl)piperidin-3-ylcarbamate (Example 16-1, 80 mg, 0.141 mmol), 10% palladium on carbon (14.97 mg, 0.014 mmol) and ammonium formate (53.2 mg, 0.844 mmol) in methanol (8 mL) was flushed with nitrogen and heated at 75° C. for 1 h. The mixture was cooled to rt, diluted with methanol and filtered through a Celite pad. The filtrate was concentrated to provide (R)-4-(3-aminopiperidin-1-yl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide as a white solid (75 mg, 98%). 1H NMR (400 MHz, methanol-d4) δ 8.13 (d, J=8.13 Hz, 1H) 7.86 (d, J=8.35 Hz, 1H) 7.68 (s, 1H) 7.29 (d, J=9.67 Hz, 1H) 6.86 (d, J=8.35 Hz, 1H) 3.54-3.72 (m, 2H) 3.24-3.53 (m, 5H) 2.88 (s, 3H) 2.11-2.29 (m, 1H) 1.92-2.11 (m, 2H) 1.44-1.73 (m, 1H). Mass spectrum m/z 435.2 (M+H)+.

후처리

  1. customwas flushed with nitrogen
  2. temperatureThe mixture was cooled to rt
  3. additiondiluted with methanol
  4. filtrationfiltered through a Celite pad
  5. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-0eb00fa424444c758b3897de50fe4b96
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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