HCID 58416747, compound → 1-(4-(2-(4-amino-1H-imidazol-1-yl)ethoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

HRID 872422Notes

Reaction equation

HRID 872422 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH2:25][CH2:26][N:27]3[CH:31]=[C:30]([N+:32]([O-])=O)[N:29]=[CH:28]3)=[CH:16][CH:15]=2)=[O:12])[N:7]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.CO.CC(O)=O.[H][H].[Pt]>[NH2:32][C:30]1[N:29]=[CH:28][N:27]([CH2:26][CH2:25][O:24][C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([NH:13][C:11]([NH:10][C:8]3[N:7]([C:35]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=3)=[O:12])=[CH:15][CH:16]=2)[CH:31]=1

Participants

5

Reactant 1

HCID 58416747HCID 58416747, compound

Product 1

HCID 584167591-(4-(2-(4-amino-1H-imidazol-1-yl)ethoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaYield 113.2%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 21877243DCM MeOH AcOHSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A solution of 1-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-(4-(2-(4-nitro-1H-imidazol-1-yl)ethoxy)naphthalen-1-yl)urea (30) (158 mg, 0.253 mmol) in DCM/MeOH/AcOH (1:1:2, 6.0 mL) was passed through a Thales H-cube (10% Pt/C Cat-Cart., 30 mm) at 1.0 ml·min−1 in full hydrogen mode at 50° C. The solvents were evaporated under reduced pressure to give 1-(4-(2-(4-amino-1H-imidazol-1-yl)ethoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (Intermediate I) as a light brown oil (150 mg, 100%): m/z 524 (M+H)+ (ES+).

Workup

  1. customat 50° C
  2. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-e38d4f70de2a4fb9a1411db2a0c2c3b7
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Reaction notes

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