Cesium carbonate → HCID 68509056, compound

HRID 1716588Notes

Reaction equation

HRID 1716588 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]([C@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[CH2:15][OH:16])[C:7]2[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:6]=2[N:5]=1.I[CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH:37]=[CH:38][CH:39]=1)[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[C:40]([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[C:33]([O:32][C:30](=[O:31])[NH:29][C:28]1[CH:27]=[C:26]2[C:39](=[CH:38][CH:37]=1)[CH2:23][CH:24]([CH2:40][N:12]1[CH2:13][CH2:14][CH:9]([N:8]3[C:7]4[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:6]=4[N:5]=[C:4]3[CH3:3])[CH:10]([CH2:15][OH:16])[CH2:11]1)[CH2:25]2)([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68509892HCID 68509892, compoundHCID 86611757HCID 86611757, compound

Product 1

HCID 68509056HCID 68509056, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-4-(2,5-Dimethylbenzimidazol-1-yl)-3-hydroxymethylpiperidine dihydrochloride (313 mg; 0.94 mmol), 3-[3-iodopropyl]-N-Boc aniline (361 mg. 1 mmol) and Cs2CO3 (1625 mg; 5 mmol) were added to CH3CN (10 mL) and the reaction mixture was heated to reflux for 14 h. After cooling to rt, the reaction mixture was filtered through Celite® and all volatiles were removed under reduced pressure to yield a brown oil from which {2-[4-(2,5-dimethyl-benzoimidazol-1-yl)-3-hydroxymethyl-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester was isolated by flash chromatography (0-10% CH3OH in EtOAc) as a heavy oil (191 mg; 39%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. filtrationthe reaction mixture was filtered through Celite®
  4. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-eb8a78464d7b47ebaea05d658e2165e4
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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