HCID 57514766, compound → HCID 57514767, compound

HRID 882059Notes

Reaction equation

HRID 882059 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:20][CH2:21][CH2:22][OH:23])=[C:6]([NH:8][C:9](=O)[CH2:10][NH:11]C(=O)OC(C)(C)C)[CH:7]=1>Cl>[NH2:11][CH2:10][C:9]1[N:20]([CH2:21][CH2:22][OH:23])[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=2[N:8]=1

Participants

3

Reactant 1

HCID 57514766HCID 57514766, compound

Product 1

HCID 57514767HCID 57514767, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 2-(5-bromo-2-(2-hydroxyethylamino)phenylamino)-2-oxoethylcarbamate (1.26 g, 3.24 mmol) was stirred in 6 N hydrochloric acid (15 mL) at 120° C. for 2 h and then concentrated. The residue was made basic with methanol/ammonium hydroxide (9:1), re-concentrated and purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (579 mg, 60%) as a yellow oil: ESI MS m/z 270 [M+H]+.

Workup

  1. concentrationconcentrated
  2. concentrationre-concentrated
  3. custompurified by column chromatography
  4. washeluting with methylene chloride

Sources & evidence

ORD record
ord-7f6e0e51572849fab5c5d6e12ffdba8f
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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