Water → HCID 50991642, compound

HRID 2192259Notes

Reaction equation

HRID 2192259 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]4)=[CH:27][CH:28]=3)[N:23]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)[CH:22]=2)=[CH:17][CH:16]=1.O>CN(C=O)C>[CH3:6][N:5]([CH3:7])[CH2:4][CH2:3][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]4)=[CH:27][CH:28]=3)[N:23]([C:43]3[CH:44]=[CH:45][N:46]=[CH:47][CH:48]=3)[CH:22]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 50991641HCID 50991641, compound

Product 1

HCID 50991642HCID 50991642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-N,N-dimethylethylamine hydrochloride (7.3 mg, 0.051 mmol) and cesium carbonate (33 mg, 0.101 mmol) were added to a mixture solution of tert-butyl 4-(3-(4-hydroxyphenyl)-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (12 mg, 0.025 mmol) in DMF (1 mL). After room temperature stirring at room temperature for 16 hours, followed by addition of water, the mixture was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound was obtained as white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe target compound was obtained as white solid

Sources & evidence

ORD record
ord-a8b11424d63c433c879e54a1b8e7bd56
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

Loading…