Potassium Carbonate → HCID 58530894, compound

HRID 2400801Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of [(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2,4-dioxo-1,3-thiazolidine (from Example 6; 0.064 mmol), 1-(2-chloroethyl)-1H-[1,2,4]triazole (0.096 mmol), K2CO3 (0.128 mmol) in DMF (1 mL) was heated in a microwave reactor at 140° C. for 10 min, then cooled to rt and concentrated in vacuo. The resultant residue was purified by silica gel chromatography (DCM/MeOH) to afford (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-[2-(1H-1,2,4-triazol-1-yl)ethyl]-1,3-thiazolidine-2,4-dione as a yellow solid.

Workup

temperaturecooled to rt
concentrationconcentrated in vacuo
customThe resultant residue was purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record: ord-e9513eeed3d9475aa5921413deabe227
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796256B2

Reaction notes

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