N-(3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide → HCID 178437952, compound

HRID 79342Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[N:29](CC3C=CC(OC)=CC=3)[N:28]=[CH:27][CH:26]=2)[N:4]=1)[CH3:2]>C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>[NH:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:5]2[C:6]3[C:11](=[C:10]([NH:12][C:13]([C:15]4[N:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]5=[N:17][CH:16]=4)=[O:14])[CH:9]=[CH:8][CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)=[N:29]1

Participants

Conditions

Temperature: 80 °C

Procedure

To N-(3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (400 mg, 0.791 mmol) was added in TFA (4 mL) and Et3SiH (2 mL). The mixture was heated at 80° C. for 3 hours, and then at 100° C. for an additional 2 hours. The reaction mixture was concentrated under reduced pressure to a residue. Purification by silica gel chromatography (EtOAc/hexanes 1:2) provided the product (197 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure to a residue
customPurification by silica gel chromatography (EtOAc/hexanes 1:2)

Sources & evidence

ORD record: ord-3c8a0942e85648d9b9fddc553f5d1eeb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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