Water → c-Fms-IN-7

HRID 79489Notes

Reaction equation

HRID 79489 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH:31]3[CH2:33][CH2:32]3)=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:34][S-:35].[Na+].O>CS(C)=O>[CH:31]1([C:16]2[C:15]3[C:19](=[CH:20][CH:21]=[CH:22][C:14]=3[NH:13][C:11]([C:8]3[N:5]4[CH:6]=[CH:7][C:2]([S:35][CH3:34])=[CH:3][C:4]4=[N:10][CH:9]=3)=[O:12])[N:18]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)[N:17]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 672599697-chloro-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67260931c-Fms-IN-7Yield 82.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 7-chloro-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (200 mg, 0.44 mmol; prepared as in Example 65, step C) and sodium methanethiolate (61 mg, 0.88 mmol) was dissolved in DMSO (2 mL). The reaction mixture was heated at 55° C. for 4 hours. The mixture was cooled to ambient temperature, transferred into water (100 mL) with stirring, and the resulting solid was collected by vacuum filtration and dried under vacuum to give the product (0.17 g). MS (ES+APCI) m/z=468.9 (M+H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationthe resulting solid was collected by vacuum filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bffbac70602c4217936d02bde27e1897
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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