HCID 24800949, compound → HCID 24801299, compound

HRID 469807Notes

Reaction equation

HRID 469807 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[O:15][C:16]3[C:22]([C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>CO.C1COCC1.[Ni]>[NH2:28][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([C:22]2[C:16]3[O:15][C:14]([NH:13][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)=[N:18][C:17]=3[CH:19]=[CH:20][CH:21]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 1

HCID 24800949HCID 24800949, compound

Product 1

HCID 24801299HCID 24801299, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.117 g (0.291 mmol) 4-[2-(3,4,5-trimethoxy-phenylamino)-benzooxazol-7-yl]-benzonitrile (example 19) in 5 ml MeOH (MeOH contains 5% NH3), 5 ml THF and 30 mg Ra—Ni (B113W EtOH, Degussa) are added. Then this mixture is hydrogenated under normal pressure for 20 h at room temperature. The reaction mixture is filtered (2 glass fiber filters used) and the filtrate is concentrated in vacuo. The residue is purified by crystallization from dichloromethane/diethyl ether to afford the title compound as a light grey solid. Rt=1.85 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: 406 (M+1)+; m.p. 208-211° C.

Workup

  1. filtrationThe reaction mixture is filtered (2 glass fiber filters used)
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by crystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-178ef5c9110e4cb5a3456be593b520e3
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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