2-Amino-3-benzyloxypyridine → HCID 59225647, compound

HRID 1426177Notes

Reaction equation

HRID 1426177 reaction equation
Cl[C:2]1[C:7]([N:8]=[C:9]=[S:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([O:18][C:19]1[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)CO>[CH2:11]([O:18][C:19]1[C:20]([NH:25][C:9]2[S:10][C:2]3[C:7]([N:8]=2)=[CH:6][CH:5]=[CH:4][N:3]=3)=[N:21][CH:22]=[CH:23][CH:24]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 903342-Amino-3-benzyloxypyridineHCID 128680882-Chloro-3-isothiocyanatopyridine

Product 1

HCID 59225647HCID 59225647, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-3-isothiocyanatopyridine (0.342 g, 2.00 mmol) and 3-(benzyloxy)pyridin-2-amine (0.401 g, 2.00 mmol) in ethylene glycol (2 mL) was heated at 120° C. for 3 hours. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by MPLC eluting with 4:1 hexane:ethyl acetate to afford the title compound as a wax. The wax was triturated with 10:1 hexanes:dichloromethane (11 mL), filtered, and dried to afford N-(3-(benzyloxy)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine (0.095 g, 14.2% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 5.30 (s, 2H), 7.03 (m, 1H), 7.32-7.43 (m, 4H), 7.50 (d, 1H), 7.60 (d, 2H), 7.93-7.97 (m, 2H), 8.35 (d, 1H), 10.71 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC
  7. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-68aba9d8e2bc46ed8b1764a4899d2fcc
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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