(S)-1-(3-chlorophenyl)ethanamine → HCID 178461847, compound

HRID 624811Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=[C:7](S(C)(=O)=O)[CH:6]=2)[CH2:3][CH2:2]1.[Cl:26][C:27]1[CH:28]=[C:29]([C@@H:33]([NH2:35])[CH3:34])[CH:30]=[CH:31][CH:32]=1>CN1C(=O)CCC1>[Cl:26][C:27]1[CH:28]=[C:29]([C@@H:33]([NH:35][C:7]2[CH:6]=[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:15]4/[C:16](=[O:21])[NH:17][C:18](=[O:20])[NH:19]/4)=[C:9]3[N:8]=2)[CH3:34])[CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To (Z)-5-((7-(cyclopropylamino)-5-(methylsulfonyl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (step c) (10 mg, 0.0275 mmol) in 200 uL NMP, was added (S)-1-(3-chlorophenyl)ethanamine (23.2 ul, 0.165 mmols) and the reaction mixture was heated in the microwave at 120° C. for 20 minutes. The mixture was concentrated and diluted with MeOH and purified by preparative HPLC to yield (S,Z)-5-((5-(1-(3-chlorophenyl)ethylamino)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione LCMS (M+1=438)

Workup

concentrationThe mixture was concentrated
additiondiluted with MeOH
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e62c7d0c17ac4b9ebc4cae48b7a802c4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

Loading…