Acetic Acid → 2-[5-(4-Azepan-1-yl-piperidin-1-yl)-2-chloro-phenyl]-1H-benzoimidazole

HRID 2047382

반응식

HRID 2047382 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([N:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[Cl:16].[NH:24]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:24]1([CH:20]2[CH2:21][CH2:22][N:17]([C:12]3[CH:13]=[CH:14][C:15]([Cl:16])=[C:10]([C:2]4[NH:3][C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[N:1]=4)[CH:11]=3)[CH2:18][CH2:19]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8119Azepane2회HCID 5049666Sodium triacetoxyborohydrideHCID 595682431-[3-(1H-benzo[d]imidazol-2-yl)-4-chlorophenyl]piperidin-4-one

생성물 1

HCID 441241202-[5-(4-Azepan-1-yl-piperidin-1-yl)-2-chloro-phenyl]-1H-benzoimidazole수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 1-[3-(1H-benzoimidazol-2-yl)-4-chloro-phenyl]-piperidin-4-one (0.10 g, 0.31 mmol) in dichloromethane (2 mL) was added azepane (0.05 mL, 0.46 mmol). After 30 min stirring at room temperature a drop of acetic acid was added, and after 1 h a further aliquot of azepane (0.05 mL, 0.46 mmol) was added, followed by sodium triacetoxyborohydride (NaB(OAc)3H) (0.10 g, 0.46 mmol). The reaction mixture was stirred at room temperature overnight, then the solvent was removed under reduced pressure, and the crude product dissolved in dichloromethane (10 mL). To the solution PS-isocyanate resin (PS-NCO) (Argonaut, loading 0.93 mmol/g) was added, then the mixture was shaken at room temperature overnight and filtered. The solvent was removed under reduced pressure to obtain a solid residue that was washed with EtOAc and Et2O then dried to give the desired product (0.07 g, 58%).

후처리

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe crude product dissolved in dichloromethane (10 mL)
  4. additionTo the solution PS-isocyanate resin (PS-NCO) (Argonaut, loading 0.93 mmol/g) was added
  5. stirringthe mixture was shaken at room temperature overnight
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customto obtain a solid residue that
  9. washwas washed with EtOAc and Et2O
  10. customthen dried

출처 및 근거

ORD 기록
ord-c92a700be4a84b15b19ba1d6ccec95b2
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592463B2

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