Hydrochloride methanol → HCID 66828480, compound

HRID 2406564Notes

Reaction equation

HRID 2406564 reaction equation
[C:1](/[C:3](=[CH:21]\[C:22]1[NH:23][CH:24]=[CH:25][N:26]=1)/[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17]COC)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2].Cl.CO>>[C:1](/[C:3](=[CH:21]\[C:22]1[NH:26][CH:25]=[CH:24][N:23]=1)/[C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2]

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 66822401HCID 66822401, compound

Product 1

HCID 66828480HCID 66828480, compoundYield 70.7%

Procedure

(E)-2-cyano-3-(1H-imidazol-2-yl)-N-(1-(4-(methoxymethoxy)phenyl)butyl)acrylamide (14.8 mg, 0.041 mmol) was dissolved into HCl/MeOH (1.25 M, 2 mL). This solution was stirred at room temperature for 18 hours. TLC showed a single product. The mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The separated organic layer was washed with sat. brine and dried with sodium sulfate and concentrated to give a light amber solid (9 mg) as crude product. The crude material was recrystallized from ethyl acetate/hexanes to afford the titled compound as a light yellow solid (6 mg) in 46% yield. 1H NMR (500 MHz, CDCl3/CD3OD) δ 7.84 (m, 1H), 7.28 (m, 1H), 7.18 (s, 1H), 6.99 (d, J=6.8, 2H), 6.82 (d, J=7.8, 2H), 3.73 (m, 2H), 1.53 (m, 2H), 1.30 (m, 2H), 0.88 (t, J=7.1, 3H). Mass spec ES+, m/z=311.1 (m+H+).

Workup

  1. customThe mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. washThe separated organic layer was washed with sat. brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b641b8b7f9f64accabb1c23503194e9b
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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