Potassium Carbonate → HCID 76021281, compound

HRID 1970183Notes

Reaction equation

[F:1][C:2]([F:40])([F:39])[C:3]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]([CH:23]4[CH2:27][CH:26]([CH2:28][OH:29])[NH:25][CH2:24]4)[CH3:22])=[N:18][C:17]3=[O:30])=[CH:12][CH:13]=2)[CH:8]=[N:7]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:48][C:49]([NH2:51])=[O:50]>CN(C=O)C>[F:40][C:2]([F:39])([F:1])[C:3]1[CH:34]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:32]=[CH:31][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]([CH3:22])[CH:23]4[CH2:24][N:25]([CH2:48][C:49]([NH2:51])=[O:50])[CH:26]([CH2:28][OH:29])[CH2:27]4)=[N:18][C:17]3=[O:30])=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-[1-(2,4-Bis-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-[(5-hydroxymethyl-pyrrolidin-3-yl)-methyl-amino]-thiazol-4-one (20 mg, 0.034 mmol) (Example 43) (30 mg, 0.051 mmol) in DMF (1 mL) was added potassium carbonate (11 mg, 0.072 mmol) followed by 2-Bromo-acetamide (30 mg, 0.22 mmol). The reaction mixture was stirred at 70° C. for 1 hour and partitioned between water and dichloromethane. The dichloromethane layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (100% ethyl acetate) to yield the title compound (24 mg, 72%).

Workup

custompartitioned between water and dichloromethane
washThe dichloromethane layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent evaporated in vacuo
customto yield a crude solid
customThe crude solid was purified via flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record: ord-8be3e4739045437f8b19a78e5fb49616
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426604B2

Reaction notes

Loading…