tert-Butylimino-tri(pyrrolidino)phosphorane → {3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester

HRID 896318Notes

Reaction equation

HRID 896318 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:17])([CH3:4])([CH3:3])[CH3:2].CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.Cl[CH2:41][C:42]1[N:46]([CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])[C:45]2[CH:52]=[CH:53][C:54]([C:56]#[N:57])=[CH:55][C:44]=2[N:43]=1>C(Cl)Cl.CCOCC>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:41][C:42]2[N:46]([CH2:47][CH2:48][CH:49]([CH3:51])[CH3:50])[C:45]3[CH:52]=[CH:53][C:54]([C:56]#[N:57])=[CH:55][C:44]=3[N:43]=2)[C:9]1=[O:17])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 20814117Tert-butyl (2-oxo-2,3-dihydrobenzimidazol-1-yl)acetateHCID 223493092-(Chloromethyl)-1-isopentyl-benzimidazole-5-carbonitrile

Product 1

HCID 20814119{3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl esterYield 209.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid tert-butyl Ester (399 mg, 1.61 mmol) in CH2Cl2 (15 ml) was trreated with BTPP and then treated with 2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (400 mg, 1.53 mmol). The reaction was stirred for 25 min then the mixture was diluted with ether and washed with water. The organic layer was dried over MgSO4, concentrated and the residue purified by column chromatography with gradient elution using first 1:1 EtOAc in hexanes then 2:1 EtOAc in hexanes to give 1.52 g (99%) of {3-[5-Cyano-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester as a white solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue purified by column chromatography with gradient elution

Sources & evidence

ORD record
ord-b9cb6dc9968f4650b566bb3a0c077233
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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