Bis-(1H-imidazol-2-YL)-methanone → HCID 24890086, compound

HRID 562506Notes

Reaction equation

HRID 562506 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][C:18]=4[Cl:26])[N:12]=[CH:11][C:10]=3[N:9]3[CH:27]=[N:28][N:29]=[C:8]3[C@H:7]2[CH2:30][CH3:31])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(C1NC=CN=1)([C:34]1[NH:35]C=CN=1)=O>CN(C=O)C>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:25]=[CH:24][C:20]([C:21]([NH:35][CH3:34])=[O:22])=[CH:19][C:18]=4[Cl:26])[N:12]=[CH:11][C:10]=3[N:9]3[CH:27]=[N:28][N:29]=[C:8]3[C@H:7]2[CH2:30][CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 248899274-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-ylamino)-3-chlorobenzoic acid

Product 1

HCID 24890086HCID 24890086, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-ylamino)-3-chlorobenzoic acid (I-3) (27 mg) was dissolved in DMF (0.4 ml) and treated with carbonyl diimidazole (12 mg, 0.077 mmol) and the mixture stirred at RT for 90 min. The solution was cooled in an ice bath and methylamine gas bubbled in for 2 min. The mixture was stirred at RT for 2 hours, evaporated under reduced pressure and purified by chromatography to give 4-((R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-ylamino)-3-chloro-N-methylbenzamide (15 mg) as a colourless solid.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. custommethylamine gas bubbled in for 2 min
  3. stirringThe mixture was stirred at RT for 2 hours
  4. customevaporated under reduced pressure
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-029b9444aca44287bb7394af3ab80e8b
Source dataset
uspto-grants-2011_11
Patent number
US08067417B2

Reaction notes

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