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Ethanol → (3S,6R)-1-[2-amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide

HRID 2367488
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HRID 2367488 반응식
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([NH:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[C:25](F)[CH:24]=2)[N:3]=1.CCO.CCN(C(C)C)C(C)C.[NH2:44][NH2:45]>O.CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([NH:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:23]2[CH:24]=[C:25]3[C:26]([C:29]([NH2:30])=[N:44][NH:45]3)=[CH:27][CH:28]=2)[N:3]=1
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참가 물질

7

반응물 4

HCID 702EthanolHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 58504505(3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide

생성물 1

HCID 58504727(3S,6R)-1-[2-amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide수율 45.8%

시약·촉매·용매

2
HCID 887Methanol용매HCID 962Water용매

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온도
110 °C

실험 절차

Into a microwave tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide (174 mg, 0.412 mmol), 5 mL of EtOH, Hunig's base (0.288 mL, 1.647 mmol), and hydrazine anhydrous (0.078 mL, 2.471 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid and the yellow solution were carefully separated due to the black solid is heavier than yellow solution. Water (20 mL) was added to the yellow solution, and a solid formed. The solid was filtered and washed by water, dried in vacuum, and then treated with EtOAc and CH3OH. The solid in the solvent was filtered, washed by EtOAc, and dried in vacuum to afford the title compound (82 mg) as a light yellow solid. LC-MS (ES) m/z=435 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.14 (m, 3H), 1.65 (m, 12H), 2.14-2.33 (m, 1H), 2.76-3.08 (m, 1H), 3.93-4.12 (m, 1H), 5.38 (s, 2H), 6.07 (s, 2H), 6.57 (s, 1H), 7.57 (m, 1H), 7.69 (m, 1H), 7.87 (m, 1H), 7.94 (s, 1H), 11.49 (s, 1H).

후처리

  1. customa solid formed
  2. filtrationThe solid was filtered
  3. washwashed by water
  4. customdried in vacuum
  5. additiontreated with EtOAc and CH3OH
  6. filtrationThe solid in the solvent was filtered
  7. washwashed by EtOAc
  8. customdried in vacuum

출처 및 근거

ORD 기록
ord-cb8382e6b6424038b72cddfe0d7d5b04
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697685B2

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