Water → HCID 16224070, compound

HRID 1517638Notes

Reaction equation

HRID 1517638 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][NH:22]3)=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:36](Cl)=[O:37])[CH2:32][CH2:31]1.O>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:36]([N:33]1[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]1)=[O:37])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 11256560N'-(5-tert-Butyl-2,3-dihydro-1H-inden-1-yl)-N-1H-indazol-4-ylcarbamimidic acid

Product 1

HCID 16224070HCID 16224070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Example 56J (240 mg, 0.69 mmol) in N,N-dimethylformamide (5 mL) was treated with 60% NaH (45 mg, 1.13 mmol) and stirred at room temperature for 15 min. 4-methylpiperazine carbonyl chloride (1.64 mmol) was then added, and the reaction mixture was stirred overnight at 80° C. It was then cooled to room temperature and poured into H2O, and the resulting precipitate was collected by filtration. Chromatography on silica gel (eluted with 97:3 CH2Cl2-methanol) afforded the desired product. 1H NMR (d6-DMSO) 67 8.59 (s, 1H), 8.07 (s, 1H), 7.72 (d, J=7.5 Hz, 1H), 7.28 (m, 3H), 7.17 (d, J=7.5 Hz, 1H), 6.66 (d, J=7.5 Hz, 1H), 5.17 (m, 1H), 4.44 (m, 2H), 3.48 (m, 2H), 3.02 (m, 1H), 2.90 (m, 1H), 2.81 (m, 1H), 2.53 (s, 3H), 2.42 (m, 1H), 1.80 (m, 1H), 1.27 (s, 9H). MS (DCI) m/z 475 (M+H). C27H34N6O2.0.5H2O: C, 67.06; H, 7.29; N, 17.38. Found: C, 66.87; H, 7.22; N, 17.04.

Workup

  1. stirringthe reaction mixture was stirred overnight at 80° C
  2. temperatureIt was then cooled to room temperature
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-ceb6e87c446d4ff5941d9eb91efa36ee
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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