Ethyl Acetate → HCID 178493063, compound

HRID 469811Notes

Reaction equation

HRID 469811 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[O:15][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[NH:30][CH:31]=O.CCOC(C)=O>C(O)(=O)C>[NH:30]1[C:3]2[CH:4]=[CH:5][C:6]([C:8]3[C:16]4[O:15][C:14]([NH:17][C:18]5[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=5)=[N:13][C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:7][C:2]=2[N:1]=[CH:31]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86637872HCID 86637872, compound

Product 1

HCID 178493063HCID 178493063, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.182 g (0.243 mmol) N-{2-amino-4-[2-(3,4,5-trimethoxy-phenylamino)-benzooxazol-7-yl]-phenyl}-formamide in 3 ml acetic acid is stirred at 100° C. for 1 h. Then EtOAc is added to the reaction mixture and the organic layer is washed with 4N NaOH solution (2×) and with water (2×), dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, EtOAc=>EtOAc:MeOH=95:5) to afford the title compound as an orange solid. Rt=1.86 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 417 (M+1)+; m.p. 150-156° C.

Workup

  1. washthe organic layer is washed with 4N NaOH solution (2×) and with water (2×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is purified by chromatography (silicagel, EtOAc=>EtOAc:MeOH=95:5)

Sources & evidence

ORD record
ord-d0fb392e5ec7451b9ecc7ee9ce433c16
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

Loading…