Sodium Bicarbonate → HCID 178497319, compound

HRID 1644599Notes

Reaction equation

HRID 1644599 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:29])[CH3:28])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][C:20]([C:23]#N)=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](=O)([O-])[OH:31].[Na+].Cl.C[OH:37]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH:27]([CH3:28])[CH3:29])=[C:13]([C:15]2[NH:25][C:18]3=[N:19][C:20]([C:23]([O:31][CH3:30])=[O:37])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 178458527HCID 178458527, compound

Product 1

HCID 178497319HCID 178497319, compoundYield 61%

Procedure

A solution of 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine-5-carbonitrile (60 mg) in hydrochloric acid-methanol (5 ml) was heated under reflux for 6 hr. The reaction mixture was adjusted with aqueous sodium hydrogencarbonate solution to pH 8, and extracted with ethyl acetate. The extract was washed with water; dried over magnesium sulfate and concentrated. The obtained crude crystals were washed with ethanol to give the title compound (40 mg, yield 61%) as colorless crystals. purity 95%. M+H: 418. 1H NMR (CDCl3) δ: 1.50 (6H, d, J=6.2 Hz), 4.06 (3H, s), 4.75-4.82 (1H, m), 5.17 (2H, s), 7.02-7.07 (1H, m), 7.10-7.15 (1H, m), 7.31-7.50 (5H, m), 8.12-8.22 (3H, m), 11.17 (1H, s).

Workup

  1. temperatureunder reflux for 6 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude crystals
  7. washwere washed with ethanol

Sources & evidence

ORD record
ord-a2c5a21170e4472e8c98c7a237584907
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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