Morpholine → N-[5-(cycloheptylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(morpholin-4-ylmethyl)benzamide

HRID 2382863Notes

Reaction equation

HRID 2382863 reaction equation
[CH:1]1([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH2:18])[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[CH:1]1([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:25](=[O:26])[C:24]4[CH:28]=[CH:29][C:21]([CH2:20][N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[CH:22][CH:23]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 25216187HCID 25216187, compound

Product 1

HCID 25214734N-[5-(cycloheptylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(morpholin-4-ylmethyl)benzamideYield 40.1%

Conditions

Temperature
60 °C

Procedure

The title compound was prepared following procedure described for intermediate B1, but starting from N5-cycloheptyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A10), 123 mg; 0.50 mmol; 1.0 eq.) and 4-(chloromethyl)benzoyl chloride (142 mg; 0.75 mmol; 1.5 eq.). Solvents were removed under reduced pressure to yield a gummy solid that was resuspended in morpholine (1.74 g; 20.0 mmol; 10.0 eq.) and the mixture was stirred at 60° C. for 2 h. After this time, reaction mixture was cooled down to rt, solvents were evaporated under reduced pressure and the residue washed with Et2O (4×5 mL). A solid crystallized in the Et2O phase which, after filtration, gave the title compound as a white solid (90 mg, 40%). HPLC, Rt: 3.99 min. (purity 98.9%). LC/MS, M+(ESI): 423.1, M−(ESI): 421.1.

Workup

  1. customThe title compound was prepared following procedure
  2. customSolvents were removed under reduced pressure
  3. customto yield a gummy solid
  4. customAfter this time, reaction mixture
  5. temperaturewas cooled down to rt
  6. customsolvents were evaporated under reduced pressure
  7. washthe residue washed with Et2O (4×5 mL)
  8. customA solid crystallized in the Et2O phase which
  9. filtrationafter filtration

Sources & evidence

ORD record
ord-c6db17678f9f4083bfc4e1495969dd98
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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