Potassium Hydroxide → HCID 117667602, compound

HRID 712586Notes

Reaction equation

HRID 712586 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.ClC(Cl)(Cl)[C:14]([N:16]=C=O)=[O:15].[OH-].[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:14]([NH2:16])=[O:15])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 76400Trichloroacetyl isocyanateHCID 179301266-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 117667602HCID 117667602, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 6-bromo-1,2,3,4-tetrahydro-[1,8]naphthyridine (6.4 g, 30.0 mmol) in DCM (75 mL) is added a trichloroacetyl isocyanate (3.8 mL, 31.5 mmol). After stirring for 1 h at 0° C., a solution of methanolic KOH (1M, 10 mL) is added. The resulting mixture is allowed to warm and stir at room temperature for 16 h. The reaction is concentrated and purified by silica gel column (0-100% EtOAc in heptane) to afford the title compound (7.4 g).

Workup

  1. temperatureto warm
  2. stirringstir at room temperature for 16 h
  3. concentrationThe reaction is concentrated
  4. custompurified by silica gel column (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-10fb7eb43d054d6da54d6dc2c3f65a8e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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