1,1'-Carbonyldiimidazole → tert-Butyl 4-(1-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

HRID 2069062Notes

Reaction equation

HRID 2069062 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.[NH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([O:41][CH2:42][CH:43]([C:45]2[CH:50]=[CH:49][N:48]=[C:47]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:46]=2)[CH3:44])=[CH:33][CH:32]=1>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:23](=[O:24])[NH:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]([O:41][CH2:42][CH:43]([C:45]3[CH:50]=[CH:49][N:48]=[C:47]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH:46]=3)[CH3:44])=[CH:33][CH:32]=2)[N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 58532582tert-Butyl 4-(1-(4-aminonaphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamate

Product 1

HCID 68313493tert-Butyl 4-(1-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)propan-2-yl)pyridin-2-ylcarbamateYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (5) 612 mg, 2.67 mmol) in DCM (2.0 mL) was added dropwise over 1.5 hr to a suspension of CDI (433 mg, 2.67 mmol) in DCM (2.0 mL) under nitrogen and the solution was stirred at RT for 1 hr. A solution of the naphthyl amine (55) (700 mg, 1.78 mmol) in DCM (4.0 mL) was added in a single portion and the solution was stirred for 16 hr, during which time a precipitate formed. The reaction mixture was taken up in DCM (10 mL) and purified by flash column chromatography (SiO2, 80 g, 0-20% EtOAc in isohexane, gradient elution) to afford the title compound (56) (0.59 g, 50%): m/z 649 (M+H)+ (ES+)

Workup

  1. stirringthe solution was stirred for 16 hr, during which time a precipitate
  2. customformed
  3. custompurified by flash column chromatography (SiO2, 80 g, 0-20% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-4e2af65faeb644baa7bfe0468370f0fa
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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