Pyridine → HCID 59437552, compound

HRID 2382899Notes

Reaction equation

HRID 2382899 reaction equation
C1CC([NH:7][C:8]2[N:17]=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([NH2:16])[N:10]3[N:9]=2)CCC1.N1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[N:25]1([CH2:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1.Cl[CH2:41]Cl>>[CH:19]1([NH:16][C:15]2[N:10]3[N:9]=[C:8]([NH:7][C:35](=[O:36])[C:34]4[CH:38]=[CH:39][C:31]([CH2:30][N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)=[CH:32][CH:33]=4)[N:17]=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:41][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 21706342HCID 21706342, compoundHCID 67535987HCID 67535987, compound

Product 1

HCID 59437552HCID 59437552, compoundYield 10%

Procedure

To a reaction vessel containing N-5-cyclohexyl-[1,2,4]triazolo[1,5-a]pyridine-2,5-diamine (69 mg, 0.3 mmol, 1 eq.) and pyridine (63 μL, 1.2 mmol, 4 eq.) in dichloromethane (1 mL) was added 4-(pyrrolidin-1-ylmethyl)benzoyl chloride hydrochloride (142 mg, 0.6 mmol, 2 eq., prepared from 4-pyrrolidin-1-ylmethyl-benzoic acid, catalytic DMF and oxalyl chloride in DCM) as a solution in dichloromethane (2 mL), dropwise. The vessel was capped and heated to reflux for approximately 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a beige solid (12.4 mg, 10%). HPLC, Rt: 3.50 min (purity: 100%). LC/MS M+(ESI): 419.2, M−(ESI) 417.2.

Workup

  1. customThe vessel was capped
  2. temperatureheated
  3. temperatureto reflux for approximately 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue dissolved in DMSO (1.5 mL)
  7. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-bb92275ffbfd4e03a13fb5a889672280
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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