m-Anisoyl chloride → HCID 136063643, compound

HRID 2382793Notes

Reaction equation

[NH2:1][C:2]1[N:22]=[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[N:11](C(OC(C)(C)C)=O)[CH:12]=[CH:13][CH:14]=3)[N:4]2[N:3]=1.[C:23](Cl)(=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1>>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:23]([NH:1][C:2]1[N:22]=[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[NH:11][CH:12]=[CH:13][CH:14]=3)[N:4]2[N:3]=1)=[O:32]

Participants

Reactant 2

HCID 74374m-Anisoyl chloride

HCID 25216183HCID 25216183, compound

Product 1

HCID 136063643HCID 136063643, compoundYield 41%

Procedure

The title compound was prepared following procedure described for intermediate B1, but starting from tert-butyl 2-(2-amino[1,2,4]triazolo[1,5-a]pyridin-5-yl)-1H-pyrrole-1-carboxylate ((A6), 50 mg; 0.17 mmol; 1.0 eq.) and m-anisoyl chloride (57 mg; 0.33 mmol; 2.0 eq.). Further treatment with a DCM/TFA solution (2:1) and purification by flash chromatography on silica (EtOAc/c-Hex, gradient from 50:60 to 80:20) gave the title compound as a white solid (23.1 mg, 41%). HPLC, Rt: 3.40 min. (purity 94.7%). LC/MS, M+(ESI): 334.3, M+(ESI): 332.1

Workup

customThe title compound was prepared following procedure
customFurther treatment with a DCM/TFA solution (2:1) and purification by flash chromatography on silica (EtOAc/c-Hex, gradient from 50:60 to 80:20)

Sources & evidence

ORD record: ord-13b81516fa3a4b759aa15ee930bceb3b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263595B2

Reaction notes

Loading…