Sodium Iodide → HCID 178520622, compound

HRID 1695213Notes

Reaction equation

HRID 1695213 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([NH2:23])[NH:21][N:22]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1.C(N(C(C)C)CC)(C)C.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[Na+].[I-]>CC(N(C)C)=O>[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[C:20]([NH:23][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[NH:21][N:22]=3)=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 178507269HCID 178507269, compound

Product 1

HCID 178520622HCID 178520622, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromovaleryl chloride (80 μL, 0.60 mmol) in DMA (1 mL) cooled at 0° C. a solution of 5-(1H-Indol-5-yl)-2H-pyrazol-3-ylamine (120 mg, 0.60 mmol) and diisopropylethylamine (104 μL, 1.20 mmol) in DMA (2 mL) was added. The reaction was left stirring for 1 hour at 0° C. and then piperidine (119 μL, 1.20 mmol) and NaI (90 mg, 0.60 mmol) were added and the mixture heated at 60° C. for 5 hours, when LC-MS showed complete conversion of the bromo-intermediate and the solvent was removed under reduced pressure.

Workup

  1. additionwas added
  2. waitThe reaction was left
  3. temperaturethe mixture heated at 60° C. for 5 hours
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-17ac4b7327ab48f7935ed821a1896b66
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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