Ammonia → HCID 11617104, compound

HRID 746622Notes

Reaction equation

HRID 746622 reaction equation
I([O-])(=O)(=O)=O.[Na+].[N:7]1([CH2:12][CH2:13][C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[C:23]([C:25]2[N:26]=[CH:27][S:28][CH:29]=2)=[CH2:24])[CH2:11][CH2:10][CH2:9][CH2:8]1.NN.N>O.CCO>[N:7]1([CH2:12][CH2:13][C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[CH:23]([C:25]2[N:26]=[CH:27][S:28][CH:29]=2)[CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 9321Hydrazine3×HCID 11624273HCID 11624273, compoundHCID 23667635Sodium periodate3×

Product 1

HCID 11617104HCID 11617104, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of EtOH (7 mL) and water (2 mL), sodium periodate (1.4 g, 6.62 mmol), 4-{1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-vinyl}-thiazole (225 mg, 0.66 mmol) and hydrazine (880 uL, 27 mmol) were added. The reaction was refluxed for 90 min, cooled down to room temperature and additional hydrazine (880 uL, 27 mmol) and sodium periodate (1.4 g, 6.6 mmol) were added. The reaction was refluxed for an additional hour, cooled down and additional aliquots of hydrazine (880 uL, 27 mmol) and sodium periodate (1.4 g, 6.6 mmol) were added. After refluxing overnight, water and ammonia were added (pH ˜9), which was followed by extraction with EtOAc, drying (MgSO4), filtration, and concentration in vacuo. Mass triggered preparative HPLC afforded 4-{1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-ethyl}-thiazole (Compound 19-4). MH+=343.

Workup

  1. additionwere added
  2. temperatureThe reaction was refluxed for 90 min
  3. temperatureThe reaction was refluxed for an additional hour
  4. temperaturecooled down
  5. temperatureAfter refluxing overnight
  6. extractionwas followed by extraction with EtOAc
  7. customdrying
  8. filtration(MgSO4), filtration, and concentration in vacuo

Sources & evidence

ORD record
ord-c5d61133a8734ec28bdaee1f5bd6e6a7
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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