Ethyl Acetate → HCID 16661451, compound

HRID 1426170Notes

Reaction equation

HRID 1426170 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[C:18]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH2:30][CH3:31])[N:29]=2)=[N:19][CH:20]=[C:21]([Br:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)(=O)C>C(#N)C>[CH2:9]([O:16][C:17]1[C:18]([NH:24][C:25]2[S:26][C:27]([Cl:1])=[C:28]([CH2:30][CH3:31])[N:29]=2)=[N:19][CH:20]=[C:21]([Br:23])[CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 72705641HCID 72705641, compound

Product 1

HCID 16661451HCID 16661451, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Chloropyrrolidine-2,5-dione (0.103 g, 0.769 mmol) was added to a solution of 3-(benzyloxy)-5-bromo-N-(4-ethylthiazol-2-yl)pyridin-2-amine (0.25 g, 0.641 mmol) in acetonitrile (6 mL). The reaction mixture was stirred for 1 hour and then partitioned between ether and water. The organic layer was washed with brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 6:1 hexane:ethyl acetate to afford 3-(benzyloxy)-5-bromo-N-(5-chloro-4-ethylthiazol-2-yl)pyridin-2-amine (0.154 g, 56.6% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 1.17 (t, 3H), 2.58 (q, 2H), 5.28 (s, 2H), 7.30-7.43 (m, 3H), 7.59 (d, 2H), 7.66 (s, 1H), 7.98 (s, 1H), 10.79 (bs, 1H).

Workup

  1. custompartitioned between ether and water
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by MPLC (Biotage)
  6. washeluting with 6:1 hexane

Sources & evidence

ORD record
ord-9dc51067aa984f6189b1e78a9b2c6ea2
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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