Hydrochloric Acid → HCID 59225671, compound

HRID 1426150Notes

Reaction equation

HRID 1426150 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:19][C:20]2[S:21][CH:22]=[C:23]([CH3:25])[N:24]=2)=[N:11][CH:12]=[C:13]([CH:15]=[CH:16][O:17]C)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH:16]=[O:17])[CH:12]=[N:11][C:10]=1[NH:19][C:20]1[S:21][CH:22]=[C:23]([CH3:25])[N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72237998HCID 72237998, compound

Product 1

HCID 59225671HCID 59225671, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 250 mL round-bottomed flask was charged with N-(3-(benzyloxy)-5-(2-methoxyvinyl)pyridin-2-yl)-4-methylthiazol-2-amine (1.93 g, 5.46 mmol) and THF (25 mL). 1M HCl (27.3 ml, 27.3 mmol) was added and the reaction was stirred at 50° C. overnight. The reaction was partitioned between EtOAc and water. The organic phase was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (30 to 50% EtOAc/hexanes) to afford the title compound (1.0 g, 54.0% yield) as a clear and colorless oil. 1H NMR (CDCl3) δ 9.75 (t, 1H), 8.55 (s, 1H), 7.82 (m, 1H), 7.40 (m, 5H), 6.96 (d, 1H), 6.40 (m, 1H), 5.09 (s, 2H), 3.66 (d, 2H), 2.32 (s, 3H). Mass spectrum (apci) m/z=340.1 (M+H).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel (30 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cfba6ee2a6f64d9ab6da45baf764fa03
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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