HCID 117842671, compound → HCID 117843482, compound

HRID 2209232Notes

Reaction equation

COC1C=CC([C@H]([N:11]2[C:15](=[O:16])[CH2:14][C@@H:13]([C@H:17]([O:19][C:20]3[C:21]4[N:22]([N:45]=[CH:46][CH:47]=4)[CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]5)=[CH:28][CH:27]=4)[CH:25]=3)[CH3:18])[CH2:12]2)C)=CC=1>C(O)(C(F)(F)F)=O>[N:32]1([C:29]2[CH:28]=[CH:27][C:26]([C:24]3[CH:25]=[C:20]([O:19][C@@H:17]([C@H:13]4[CH2:12][NH:11][C:15](=[O:16])[CH2:14]4)[CH3:18])[C:21]4[N:22]([N:45]=[CH:46][CH:47]=4)[CH:23]=3)=[CH:31][CH:30]=2)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 60 °C

Procedure

Tert-butyl 4-(4-(4-((R)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyridin-6-yl)phenyl)piperazine-1-carboxylate 6.15 (50 mg, 0.078 mmol) was dissolved in TFA (2.0 mL) and heated at 60° C. for 18 h. The reaction was concentrated to dryness (solvent exchange was performed with acetonitrile and toluene) and the residue was passed through a polymer-supported bicarbonate column to provide (R)-4-((R)-1-((6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 6.16, as the free base, and was used directly in the next reaction.

Workup

concentrationThe reaction was concentrated to dryness (solvent exchange was performed with acetonitrile and toluene)

Sources & evidence

ORD record: ord-0aa5cd87c5f3405388d47891e361b903
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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