Triethylamine → HCID 118005552, compound

HRID 1478489Notes

Reaction equation

HRID 1478489 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[CH2:13]([O:20][CH2:21][C:22](Cl)=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(CC)CC>C(Cl)Cl>[CH2:13]([O:20][CH2:21][C:22]([NH:11][C:5]1[CH:6]=[CH:7][C:8]([Br:10])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:12])=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 118005552HCID 118005552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl-2-amino-5-bromobenzoate (15 g, 62.6 mmol) in DCM (241 mL) at 0° C. was added benzyloxyacetyl chloride (12.5 mL, 75.1 mmol) followed by Et3N (20 mL, 144 mmol) dropwise. The resulting white suspension was stirred at room temperature for 3 hours. The mixture was then washed with saturated aqueous NH4Cl (200 mL) followed by water (200 mL). The organics were dried (Na2SO4), filtered and concentrated to dryness. The crude solid was triturated with MeOH (90 mL) and dried under vacuum to afford the title compound as a white solid.

Workup

  1. washThe mixture was then washed with saturated aqueous NH4Cl (200 mL)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude solid was triturated with MeOH (90 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-125033b6a72646be8af174de5dde96d9
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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