Toluene → HCID 135984689, compound

HRID 600588Notes

Reaction equation

HRID 600588 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[NH:11][CH:10]=[N:9][C:8]=2[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[NH:4][N:3]=1.[C:18](Cl)(Cl)=[O:19].C1(C)C=CC=CC=1>C1COCC1>[CH3:1][C:2]1[N:6]=[C:5]2[N:4]([C:18](=[O:19])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]3[N:9]=[CH:10][NH:11][C:7]=32)[N:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 178446281HCID 178446281, compound

Product 1

HCID 135984689HCID 135984689, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-methyl-1H-1,2,4-triazol-5-yl)-N-pentyl-1H-imidazol-4-amine (45 mg, 0.19 mmol) in THF (10 mL) at 0° C. was added phosgene in toluene (0.3 mL, 1.0 mmol). The reaction mixture was slowly warmed to room temperature while stirring. The reaction mixture was concentrated under reduced pressure, and the residue was purified by preparative LCMS (method A) to provide the desired product (25 mg, 50% yield) as a white powder. LCMS calculated for C12H17N6O (M+H): 261.1. found: 261.1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by preparative LCMS (method A)

Sources & evidence

ORD record
ord-ce9aaf1a57f544bab97f82343a9bb6ec
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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