Hydrochloride methanol → HCID 86663516, compound

HRID 2406560Notes

Reaction equation

HRID 2406560 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[C:9]([C:27]#[N:28])[C:10]([NH:12][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23]COC)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1.Cl.CO>CCOC(C)=O.CCCCCC>[Br:1][C:2]1[N:7]=[C:6](/[CH:8]=[C:9](\[C:27]#[N:28])/[C:10]([NH:12][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[O:11])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 86762603HCID 86762603, compound

Product 1

HCID 86663516HCID 86663516, compoundYield 161.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

3-(6-bromopyridin-2-yl)-2-cyano-N-(1-(4-(methoxymethoxy)phenyl)butyl)acrylamide (14 mg, 0.031 mmol) was dissolved into HCl/MeOH (1.25 M, 2 mL). This solution was stirred at room temperature for 18 hours. TLC (in 50% EtOAc/Hexane) 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 (20 mg) as crude product. The crude material was purified by preparative TLC to afford the title compound as a light yellow solid (12 mg) in 95% yield. 1H NMR (500 MHz, CDCl3/CD3OD) δ 7.55 (dd, J=7.8, 7.5 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.18 (d, J=7.4 Hz, 1H), 1H), 7.07 (d, J=7.4 Hz, 2H), 6.78 (s, 1H), 6.68 (d, J=8.3 Hz, 1H), 3.78 (t, J=7.6 Hz, 1H), 1.62 (m, 2H), 1.34 (m, 2H), 0.88 (t, J=7.3 Hz, 3H). 1H NMR (500 MHz, CDCl3/CD3OD) δ 161.9, 157.2, 151.4, 142.0, 140.8, 139.0, 131.9, 129.4, 128.9, 124.5, 116.5, 115.8, 115.2, 49.5, 29.2, 20.09, 13.7; Mass spec ES+; m/z=422 (m+Ma+); mp (195° C. decomposition starts). Elemental analysis: C=56.73%, H=4.51%, N=10.33%. (calc: C=57.01%, H=4.53%, N=10.50%).

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-1a088bfeb8e44dc1875a61bfac836279
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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