HCID 178431474, compound → HCID 178509782, compound

HRID 658111Notes

Reaction equation

HRID 658111 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C@@H:29]2[CH2:33][O:32]C(C)(C)[O:30]2)[C:24]=1[F:36])=[O:22])[C:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:12]>C(O)(=O)C.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C@@H:29]([OH:30])[CH2:33][OH:32])[C:24]=1[F:36])=[O:22])[C:11]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:12]

Participants

3

Reactant 1

HCID 178431474HCID 178431474, compound

Product 1

HCID 178509782HCID 178509782, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A 140 mg portion of 3-(2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-{3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluorophenyl}-3-oxopropanoyl)benzonitrile was dissolved in 5 ml of acetic acid-water (4:1) and stirred at 50° C. for 3 hours. The solvent was evaporated to carry out an azeotropic treatment using Tol. The thus formed residue was purified by a silica gel column chromatography, and the foamy substance obtained from a chloroform-methanol (10:0-9:1) eluate was recrystallized from ethyl acetate hexane to obtain 105 mg (82%) of 3-(2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-{3-[(1R)-1,2-dihydroxyethyl]-2-fluorophenyl}-3-oxopropanoyl)benzonitrile (Example 4-11).

Workup

  1. customThe solvent was evaporated
  2. customThe thus formed residue was purified by a silica gel column chromatography
  3. customthe foamy substance obtained from a chloroform-methanol (10:0-9:1) eluate
  4. customwas recrystallized from ethyl acetate hexane

Sources & evidence

ORD record
ord-93e1d5557a25400ba37d8f943671ea28
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

Loading…