Dimethylformamide → HCID 67348986, compound

HRID 1970146Notes

Reaction equation

CN(C=O)C.[Cl:6][C:7]1[CH:37]=[CH:36][C:10]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][C:17]([CH:21]=[C:22]4[S:26][C:25]([N:27]([CH3:34])[CH:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)=[N:24][C:23]4=[O:35])=[CH:18][CH:19]=3)[CH:14]=[N:13]2)=[C:9]([C:38]([F:41])([F:40])[F:39])[CH:8]=1.Br[CH2:43][CH2:44][O:45][CH3:46].C([O-])([O-])=O.[K+].[K+]>O>[Cl:6][C:7]1[CH:37]=[CH:36][C:10]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][C:17]([CH:21]=[C:22]4[S:26][C:25]([N:27]([CH:28]5[CH2:33][CH2:32][N:31]([CH2:43][CH2:44][O:45][CH3:46])[CH2:30][CH2:29]5)[CH3:34])=[N:24][C:23]4=[O:35])=[CH:18][CH:19]=3)[CH:14]=[N:13]2)=[C:9]([C:38]([F:41])([F:40])[F:39])[CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a DMF solution (1 mL) containing 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-piperidin-4-yl-amino)-thiazol-4-one (Example 16, 54 mg, 0.1 mmol) was added 1-bromo-2-methoxyethane (27.8 mg, 0.2 mmol) and K2CO3 (28 mg, 0.2 mmol). The mixture was stirred at 70° C. for 4 h, diluted with water and extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried (Na2SO4), and evaporated. The residue was purified by flash column chromatography on silica gel (EtOAc→10% MeOH/EtOAc) to afford the desired product (30 mg, 50%).

Workup

extractionextracted with EtOAc
washThe combined EtOAc extracts were washed with brine
dry with materialdried (Na2SO4)
customevaporated
customThe residue was purified by flash column chromatography on silica gel (EtOAc→10% MeOH/EtOAc)

Sources & evidence

ORD record: ord-f407b267dc5e44bebda3b6a79e2af0cb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426604B2

Reaction notes

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