Potassium Carbonate → HCID 66613353, compound

HRID 510081Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[S:28])[NH:6]2.C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]([F:40])([F:39])[CH2:37]I>CN(C)C=O>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]2[N:8]=[C:7]3[C:3]([NH:4][C:5]([S:28][CH2:37][C:36]([F:40])([F:39])[F:35])=[N:6]3)=[C:2]([NH2:1])[N:10]=2)=[N:12]1

Participants

Conditions

Temperature: 70 °C

Procedure

150 mg (0.382 mmol) of the compound from example 28 were dissolved in 2 ml of dimethylformamide, and 58 mg (0.420 mmol) of potassium carbonate were added. The mixture was heated to 70° C. for 10 min and, after cooling, 38 μl (0.382 mmol) of trifluoroethyl iodide were added and the mixture was stirred at RT for 16 h. The mixture was concentrated, and the residue was adsorbed on silica gel and purified by means of chromatography on silica gel (eluent: dichloromethane/methanol=20:1). 49 mg of the title compound were obtained (25% of theory).

Workup

temperatureafter cooling
concentrationThe mixture was concentrated
custompurified by means of chromatography on silica gel (eluent: dichloromethane/methanol=20:1)

Sources & evidence

ORD record: ord-b2c6d96b9c4b436aa25a70a8d818be3d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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