1-Ethyl-1,4-diazepane → HCID 178462581, compound

HRID 16893Notes

Reaction equation

HRID 16893 reaction equation
[CH2:1]([N:3]1[CH2:9][CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].Cl[C:11]1[N:12]=[CH:13][C:14]([C:17]([NH:19][C:20]2[NH:21][N:22]=[C:23]([CH2:25][CH2:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=3)[CH:24]=2)=[O:18])=[N:15][CH:16]=1>CS(C)=O.CO>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][C:23]2[CH:24]=[C:20]([NH:19][C:17]([C:14]3[CH:13]=[N:12][C:11]([N:6]4[CH2:7][CH2:8][CH2:9][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]4)=[CH:16][N:15]=3)=[O:18])[NH:21][N:22]=2)[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=1

Participants

5

Reactant 2

HCID 75775381-Ethyl-1,4-diazepaneHCID 178489782HCID 178489782, compound

Product 1

HCID 178462581HCID 178462581, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

1-ethyl-1,4-diazepane (205 mg, 1.60 mmol) was added to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (310 mg, 0.80 mmol) in DMSO (4.00 ml) at 25° C. The resulting solution was stirred at room temperature for 2 h. The reaction was incomplete so the temperature was increased to 60° C. and the reaction mixture was stirred for a further 15 mins. The reaction mixture was diluted with MeOH (5 ml) and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product as an orange dry film. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (228 mg, 59%) as a white solid.

Workup

  1. temperaturewas increased to 60° C.
  2. stirringthe reaction mixture was stirred for a further 15 mins
  3. customthe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness
  6. customto afford crude product as an orange dry film
  7. customThe crude product was purified by preparative HPLC
  8. additionFractions containing the desired compound
  9. customwere evaporated to dryness

Sources & evidence

ORD record
ord-dc0ac04dad9d4018afdff895f79e3cb4
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

Loading…