1,1'-Carbonyldiimidazole → 1-(4-((2-Aminopyridin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea

HRID 2067002Notes

Reaction equation

HRID 2067002 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]([C:17]1[CH:21]=[C:20]([NH2:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:18]=1)([CH3:16])([CH3:15])[CH3:14].[NH2:30][C:31]1[CH:36]=[C:35]([CH2:37][O:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]([NH2:49])=[CH:41][CH:40]=2)[CH:34]=[CH:33][N:32]=1>C(Cl)Cl>[NH2:30][C:31]1[CH:36]=[C:35]([CH2:37][O:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]([NH:49][C:1]([NH:22][C:20]3[N:19]([C:23]4[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=4)[N:18]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:21]=3)=[O:2])=[CH:41][CH:40]=2)[CH:34]=[CH:33][N:32]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 584167572-Amino-4-((4-aminonaphthalen-1-yloxy)methyl)pyridine

Product 1

HCID 584167531-(4-((2-Aminopyridin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureaYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1′-carbonyldiimidazole (CDI) (4.18 g, 25.80 mmol) in DCM (15 mL) was added dropwise under nitrogen a solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (6) (5.91 g, 25.80 mmol) in DCM (15 mL) over 40 mins. The resulting solution was stirred at RT for 1 h and then added dropwise under nitrogen to a solution of 2-amino-4-[(4-aminonaphthalen-1-yloxy)methyl]pyridine (4) (3.80 g, 12.89 mmol). The mixture was stirred overnight and the volatiles were then removed in vacuo. The crude material was purified by flash chromatography (Biotage 120 g); eluting with 0 to 6% MeOH in DCM to give 1-{4-[(2-aminopyridin-4-yl)methoxy]naphthalen-1-yl}-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea (5) (4.27 g, 63%): m/z 521 (M+H)+ (ES+).

Workup

  1. stirringThe mixture was stirred overnight
  2. customthe volatiles were then removed in vacuo
  3. customThe crude material was purified by flash chromatography (Biotage 120 g)
  4. washeluting with 0 to 6% MeOH in DCM

Sources & evidence

ORD record
ord-c5e70bf25cdb40ff80e45356621c6370
Source dataset
uspto-grants-2012_10
Patent number
US08293771B2

Reaction notes

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