Pyridine → HCID 59437496, compound

HRID 2382883Notes

Reaction equation

HRID 2382883 reaction equation
N1C=CC=CC=1.[CH:7]1([NH:13][C:14]2[N:19]3[N:20]=[C:21]([NH2:23])[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl.Cl[CH2:26][C:27]1[N:32]=[CH:31][C:30]([C:33](Cl)=[O:34])=[CH:29][CH:28]=1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(Cl)Cl.C1COCC1>[CH:7]1([NH:13][C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:33](=[O:34])[C:30]4[CH:29]=[CH:28][C:27]([CH2:26][N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[N:32][CH:31]=4)[N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8083MorpholineHCID 25216186N5-cyclohexyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamineHCID 86643869HCID 86643869, compound

Product 1

HCID 59437496HCID 59437496, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Pyridine (198 mg; 2.5 mmol; 5.0 eq.) was added to a solution of N5-cyclohexyl[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine ((A9), 116 mg; 0.50 mmol; 1.0 eq.) in DCM (2.0 mL). 6-(chloromethyl)pyridine-3-carbonyl chloride hydrochloride (190 mg; 1.0 mmol; 2.0 eq.) was added and the resulting black solution was stirred under reflux for 14 h. The solvents were evaporated to yield a black oil. Morpholine (218 mg; 2.5 mmol; 5.0 eq.) and THF (0.5 mL) were added to this residue, and the mixture was then stirred and heated at 60° C. for 12 h. Purification by RP-HPLC (Waters Sunfire™ Prep C18 OBD™ 5 μM, 100×49 mm) following a gradient starting with 20/80 (0.1% formic acid in CH3CN/0.1% formic acid in H2O) up to 95/5 in 12 min. The fractions were collected and lyophilized to give the title compound as a white powder (20 mg, 9%). HPLC, Rt: 2.11 min. (purity 100%). LC/MS, M+(ESI): 436.3.

Workup

  1. temperatureunder reflux for 14 h
  2. customThe solvents were evaporated
  3. customto yield a black oil
  4. stirringthe mixture was then stirred
  5. customPurification by RP-HPLC (Waters Sunfire™ Prep C18 OBD™ 5 μM, 100×49 mm)
  6. customThe fractions were collected

Sources & evidence

ORD record
ord-17c9a930b34843bdac828600c9566a35
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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