Isobutylamine → tert-butyl (4S)-4-[4-((2-methylpropyl)methylcarbamoyl)piperidin-1-yl]azepane-1-carboxylate

HRID 714549노트

반응식

HRID 714549 반응식
CO[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C@H:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[CH2:25]([NH2:29])[CH:26]([CH3:28])[CH3:27].[CH3:30]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:27][CH:26]([CH3:28])[CH2:25][N:29]([CH3:30])[C:3]([CH:5]1[CH2:6][CH2:7][N:8]([C@H:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:13][CH2:12]2)[CH2:9][CH2:10]1)=[O:4]

참가 물질

6

반응물 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89590036(S)-tert-Butyl 4-(4-(methoxycarbonyl)piperidin-1-yl)azepane-1-carboxylate

생성물 1

HCID 131734061tert-butyl (4S)-4-[4-((2-methylpropyl)methylcarbamoyl)piperidin-1-yl]azepane-1-carboxylate수율 35%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-butyl (4S)-4-[4-(methoxycarbonyl)piperidin-1-yl]azepane-1-carboxylate (0.3 g, 0.92 mmol) was dissolved in DMF (4 mL) and isobutylamine (0.14 g, 0.18 mL, 1.84 mmol), HATU (0.53 g, 1.38 mmol) and DIPEA (0.36 g, 0.48 mL, 2.76 mmol) were added. The reaction mixture was stirred at rt for 48 h and the solvents were removed in vacuo. The residue was partitioned between DCM and sat. NaHCO3 sol., the organic layer was washed with sat. NaCl sol. and dried (MgSO4). The solvents were removed in vacuo, and the residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 10 g, 40-63 μm, 60 Å, 12 mL per min, gradient 0% to 10% MeOH in DCM]) to give tert-butyl (4S)-4-[4-((2-methylpropyl)methylcarbamoyl)piperidin-1-yl]azepane-1-carboxylate (0.12 g, 35%) as a pale yellow gum.

후처리

  1. customthe solvents were removed in vacuo
  2. customThe residue was partitioned between DCM and sat. NaHCO3 sol.
  3. washthe organic layer was washed with sat. NaCl sol.
  4. dry with materialdried (MgSO4)
  5. customThe solvents were removed in vacuo
  6. customthe residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil 10 g, 40-63 μm, 60 Å, 12 mL per min, gradient 0% to 10% MeOH in DCM])

출처 및 근거

ORD 기록
ord-d07718dcd4a948549a633147b7ea0660
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187451B2

반응 노트

불러오는 중…