1,1'-Carbonyldiimidazole → HCID 58416754, compound

HRID 2069073Notes

Reaction equation

HRID 2069073 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][C:43]2[CH:48]=[CH:47][N:46]=[C:45]([NH2:49])[N:44]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[NH2:49][C:45]1[N:44]=[C:43]([CH2:42][O:41][C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]([NH:30][C:23]([NH:10][C:8]3[N:7]([C:11]4[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=4)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=3)=[O:24])=[CH:32][CH:33]=2)[CH:48]=[CH:47][N:46]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 584167554-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine

Product 1

HCID 58416754HCID 58416754, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (5) (0.98 g, 4.26 mmol) in DCM (4.0 mL) was added dropwise over 1 hr, to a suspension of CDI (0.69 g, 4.26 mmol) in DCM (3.0 mL) and the mixture was stirred at RT for 2 hr. This solution was then added dropwise to a solution of the naphthylamine (71) (0.90 g, 2.37 mmol) in DCM (10 mL), such that after each 1.0 mL aliquot was added, the reaction was stirred for 1 hr. The reaction was quenched with MeOH (20 mL), and silica was added (20 g) and the volatiles were evaporated in vacuo. The residue was subjected to purification by column chromatography (100 g, 50 to 100% EtOAc in isohexane, gradient elution). The resulting product was triturated from DCM (20 mL) and the solid collected, and washed with diethyl ether (50 mL) to give the title compound (Intermediate P) as a purple solid (0.48 g, 38%): m/z 523 (M+H)+ (ES+).

Workup

  1. additionsuch that after each 1.0 mL aliquot was added
  2. stirringthe reaction was stirred for 1 hr
  3. customThe reaction was quenched with MeOH (20 mL), and silica
  4. additionwas added (20 g)
  5. customthe volatiles were evaporated in vacuo
  6. customThe residue was subjected to purification by column chromatography (100 g, 50 to 100% EtOAc in isohexane, gradient elution)
  7. customThe resulting product was triturated from DCM (20 mL)
  8. customthe solid collected
  9. washwashed with diethyl ether (50 mL)

Sources & evidence

ORD record
ord-63531179a1b943d9b10d35582bc61bf7
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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