1-Methylcyclopropanecarboxylic acid → (3aS,7aS)-1-(1'-(1-methylcyclopropanecarbonyl)-1,4'-bipiperidin-4-yl)hexahydro-1H-benzo[d]imidazol-2(3H)-one

HRID 2421078노트

반응식

HRID 2421078 반응식
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1([C:29]([OH:31])=O)[CH2:28][CH2:27]1.C(N(CC)C(C)C)(C)C.[N:41]1([CH:57]2[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]2)[CH2:46][CH2:45][CH:44]([N:47]2[C@H:51]3[CH2:52][CH2:53][CH2:54][CH2:55][C@@H:50]3[NH:49][C:48]2=[O:56])[CH2:43][CH2:42]1>CC(N(C)C)=O>[CH3:25][C:26]1([C:29]([N:60]2[CH2:61][CH2:62][CH:57]([N:41]3[CH2:42][CH2:43][CH:44]([N:47]4[C@H:51]5[CH2:52][CH2:53][CH2:54][CH2:55][C@@H:50]5[NH:49][C:48]4=[O:56])[CH2:45][CH2:46]3)[CH2:58][CH2:59]2)=[O:31])[CH2:28][CH2:27]1

참가 물질

6

반응물 4

HCID 813261-Methylcyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24882730(3aS,7aS)-1-[1-(4-piperidyl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

생성물 1

HCID 24883160(3aS,7aS)-1-(1'-(1-methylcyclopropanecarbonyl)-1,4'-bipiperidin-4-yl)hexahydro-1H-benzo[d]imidazol-2(3H)-one수율 20.6%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

HBTU (284 mg, 0.75 mmol) was added to a solution of 1-methylcyclopropanecarboxylic acid (75 mg, 0.75 mmol), N,N-diisopropylethyl amine (194 mg, 1.50 mmol) and (3aS,7aS)-1-(1,4′-bipiperidin-4-yl)hexahydro-1H-benzo[d]imidazol-2(3H)-one (153.22 mg, 0.50 mmol) in DMA (10 mL) and stirred at room temperature for overnight. Concentrated in vacuo, diluted in dichloromethane (50 ml) and washed with sat. NaHCO3 (10 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by high pH Prep LCMS to give the titled compound (40 mg, 20.6%). 1H NMR (400 MHz, CHLOROFORM-D): δ ppm 0.51-0.59 (m, 2H) 0.86-0.94 (m, 2H) 1.30 (s, 3H) 1.33-1.45 (m, 6H) 1.68 (s, 1H) 1.74-1.84 (m, 7H) 1.96 (d, J=10.16 Hz, 1H) 2.21-2.32 (m, 3H) 2.48 (t, J=11.13 Hz, 1H) 2.76 (s, 1H) 2.92-3.03 (m, 4H) 3.71-3.81 (m, 1H) 4.49 (s, 3H). MS (M+1): 389.2

후처리

  1. concentrationConcentrated in vacuo
  2. additiondiluted in dichloromethane (50 ml)
  3. washwashed with sat. NaHCO3 (10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by high pH Prep LCMS

출처 및 근거

ORD 기록
ord-1ac37ebd115f456196783f2d95cb1a8a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956069B2

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