Cyclopentylamine → HCID 59437556, compound

HRID 2382887Notes

Reaction equation

HRID 2382887 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[O:13])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>C(O)CCC>[CH:19]1([NH:24][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12]([C:14]4[O:15][CH:16]=[CH:17][CH:18]=4)=[O:13])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 86643871HCID 86643871, compound

Product 1

HCID 59437556HCID 59437556, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A sealed vessel containing furan-2-carboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide (61 mg, 0.20 mmol, 1 mol eq.), cyclopentylamine (26 mg, 0.30 mmol, 1.5 mol eq.), di-iso-propylethylamine (60 pt, 0.32 mmol, 1.6 mol eq.) and n-butanol (0.75 ml) was irradiated at 220° C., with stirring, for 20 minutes. The solvent was removed in vacuo and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (28.4 mg, 46%). HPLC, Rt: 2.32 min (purity: 97%). LC/MS M+(ESI): 312.3.

Workup

  1. customwas irradiated at 220° C.
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DMSO (1.5 mL)
  4. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-2f7f7184d1fb42ec92f5943530b1c9ce
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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