Hydrochloric Acid → 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile

HRID 555286노트

반응식

HRID 555286 반응식
[C:1]([CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([OH:16])=O)=[CH:13][C:8]=2[N:7]=[CH:6]1)#[N:2].C1C=CC2N(O)N=NC=2C=1.Cl.CC[N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32].CCN=C=NCCCN(C)C.Cl.CN([CH:52]=[O:53])C>>[OH:53][CH:52]1[CH2:35][CH:34]2[N:30]([C:14]([C:12]3[CH:11]=[CH:10][C:9]4[N:5]([CH2:4][CH2:3][C:1]#[N:2])[CH:6]=[N:7][C:8]=4[CH:13]=3)=[O:16])[CH:31]([CH2:32][CH2:36]2)[CH2:33]1

참가 물질

7

반응물 6

HCID 313Hydrochloric Acid2회HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669873251-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid

생성물 1

HCID 669878143-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile수율 67%

실험 절차

To a solution of 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid (0.25 g, 1.16 mmol) in DMF (2.5 mL) was added with stirring HOBt (0.17 g, 1.27 mmol) followed by exo-nortropinol hydrochloride (0.21 g, 1.27 mmol), DIPEA (0.45 g, 3.48 mmol). EDCl.HCl was then added and it was stirred at room temperature for 12 h. The solvent was then evaporated and to the residue diluted with water (5 mL) and extracted with CH2Cl2. The organic phase was washed with brine solution, dried (Na2SO4) and the solvent evaporated. The residue was purified by preparative HPLC which afforded 0.26 g (67%) of 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile. MS-ESI m/z 325 (M+1).

후처리

  1. customThe solvent was then evaporated and to the residue
  2. additiondiluted with water (5 mL)
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with brine solution
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customThe residue was purified by preparative HPLC which

출처 및 근거

ORD 기록
ord-70da5a04389a435099296b11e06fea50
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053431B2

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