Acetic Acid → HCID 178490890, compound

HRID 1370139Notes

Reaction equation

HRID 1370139 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:5][N:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[N:8]([C@H:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2)[C:7]1=[O:24].[C:30](O)(=[O:32])[CH3:31].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:30]([O:23][C@@H:20]1[CH2:19][CH2:18][C@H:17]([N:8]2[C:9]3=[N:10][CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[C:14]3[N:6]([CH2:5][C:4]3[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:2]([Cl:1])[CH:3]=3)[C:7]2=[O:24])[CH2:22][CH2:21]1)(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178490888HCID 178490888, compound

Product 1

HCID 178490890HCID 178490890, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-chloro-4-methoxybenzyl)-6-cyano-3-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (500 mg), acetic acid (76.9 mg) and diethyl azodicarboxylate (221 mg) in anhydrous tetrahydrofuran (5 mL) was added triphenylphosphine (334 mg). The mixture was stirred at ambient temperature for overnight. The mixture was evaporated in vacuo, and the residue was purified by a silica gel column chromatography eluting with a mixture of n-hexane and ethyl acetate (3:1) to give 3-(cis-4-acetoxycyclohexyl)-1-(3-chloro-4-methoxybenzyl)-6-cyano-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one (150 mg) as a pale yellow gum.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by a silica gel column chromatography
  3. washeluting with a mixture of n-hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-5db37497d52142f59cba3c692aeaaf7e
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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