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

HRID 39336Notes

Reaction equation

HRID 39336 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-e910bacf3d9a4fcd95d689b21d523c0a
Source dataset
uspto-grants-2013_09
Patent number
US08524902B2

Reaction notes

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