HCID 67451632, compound → HCID 67451369, compound

HRID 571104Notes

Reaction equation

HRID 571104 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([N+:25]([O-])=O)=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[O:6])[CH2:3][CH2:2]1.[H][H]>CO.CC(O)=O.[Pt]>[NH2:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)=[O:6])[CH:13]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 2

HCID 67451632HCID 67451632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67451369HCID 67451369, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1-cyclopropyl-3-(4-((4-nitronaphthalen-1-yl)oxy)pyridin-2-yl)urea (118 mg, 0.324 mmol) in a mixture of MeOH (20 mL) and AcOH (0.5 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, 25° C., 70 mm, 10% Pt—C Cat-Cart, full hydrogen mode). The reaction mixture was evaporated in vacuo and the residue was partitioned between DCM (20 mL) and saturated aq. NaHCO3 (10 mL). The organic phase was separated and was washed with brine (10 mL), and then dried and evaporated in vacuo to afford the title compound, Intermediate D3, as a brown solid (90 mg, 83%); Rt 1.52 min (Method 2); m/z 335 (M+H)+ (ES+).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was partitioned between DCM (20 mL) and saturated aq. NaHCO3 (10 mL)
  3. customThe organic phase was separated
  4. washwas washed with brine (10 mL)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-db22f1d7e50846669972f4d5dc213268
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

Loading…