Triethylamine → HCID 178434360, compound

HRID 245640Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:31]([CH3:32])=[N:30][NH:29][C:5]2=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:13]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[O:8][C:7]2=[O:28].Cl.[C:34]1([NH2:40])([CH:37]2[CH2:39][CH2:38]2)[CH2:36][CH2:35]1.C(N(CC)CC)C>CN(C)C=O>[C:34]1([NH:40][C:7]([C:6]2[C:11]([NH:10][C:9]([C:12]3[N:13]([C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=4)[N:14]=[C:15]([C:17]([F:18])([F:20])[F:19])[CH:16]=3)=[O:8])=[C:2]([Cl:1])[CH:3]=[C:4]3[C:5]=2[NH:29][N:30]=[C:31]3[CH3:32])=[O:28])([CH:37]2[CH2:39][CH2:38]2)[CH2:36][CH2:35]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 150 mg (0.25 mmol) of the above 5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 3 mL of N,N-dimethylformamide is added 100 mg (0.75 mmol) of bicyclopropyl-1-ylamine hydrochloride and 104 μL (0.75 mmol) of triethylamine. The reaction is stirred at 50° C. for 24 hours and then concentrated in vacuo. The residue is taken-up with acetone and after filtration the filtrate is evaporated. Purification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 3:2) affords 70 mg (48%) of a solid; LC/MS:578/580 (M+H)+, m.p.: 228-229° C.

Workup

concentrationconcentrated in vacuo
filtrationafter filtration the filtrate
customis evaporated
customPurification of the residue by flash chromatography (SiO2, hexanes/ethyl acetate 3:2)

Sources & evidence

ORD record: ord-1f561d7114d24eccbac40f215ea139b5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658801B2

Reaction notes

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