Diisopropylethylamine → HCID 178522492, compound

HRID 2382865Notes

Reaction equation

HRID 2382865 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1.CCN(C(C)C)C(C)C>C(O)CCC>[OH:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([NH:21][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 25212516N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamideHCID 178479278HCID 178479278, compound

Product 1

HCID 178522492HCID 178522492, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B4), 100 mg; 0.37 mmol; 1.0 eq.), trans-4-aminocyclohexanol hydrochloride (ABCR), 277 mg; 1.83 mmol; 5.0 eq.), DIEA (472 mg; 3.65 mmol; 10.0 eq.) in n-butanol (1.0 mL) was heated at 220° C. for 20 min under microwave irradiation. The reaction mixture was directly purified by reverse phase chromatography (Starting with water then up to 60% ACN in water in 40 min.). The title compound was isolated after lyophilisation as a white powder (31 mg, 24%). HPLC, Rt: 1.77 min. (purity 80.2%). LC/MS, M+(ESI): 353.1, M−(ESI): 351.1.

Workup

  1. customThe reaction mixture was directly purified by reverse phase chromatography (

Sources & evidence

ORD record
ord-29238990b2ca44389d9a9559e09063c5
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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