Thionyl Chloride → HCID 178527412, compound

HRID 1506180Notes

Reaction equation

HRID 1506180 reaction equation
[C:1]1([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][S:20]([OH:23])(=[O:22])=O)[CH2:15][CH2:14]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2.S(Cl)(Cl)=O.C([N:31](CC)[CH:32]([CH3:34])[CH3:33])(C)C.C1(N)CC1>ClCCl.CN(C)C=O.O>[C:1]1([C@H:13]2[CH2:14][CH2:15][C@H:16]([CH2:19][S:20]([NH:31][CH:32]3[CH2:34][CH2:33]3)(=[O:22])=[O:23])[CH2:17][CH2:18]2)[N:2]=[N:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][NH:12][C:7]=1[N:6]=[CH:5]2

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 178527649HCID 178527649, compound

Product 1

HCID 178527412HCID 178527412, compoundYield 7.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

[trans-4-(7H-Pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]methanesulfonic acid (17.8 mg, 0.0530 mmol) in dichloromethane (1.5 mL) and N,N-dimethylformamide (1.8 mL) was stirred with thionyl chloride (0.00770 mL, 0.106 mmol) at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (1.0 mL) and mixed with N,N-diisopropylethylamine (0.0923 mL, 0.530 mmol) and cyclopropylamine (0.0148 mL, 0.212 mmol) under cooling with ice and then stirred at room temperature for 1 day. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl hexane/acetate=4/1→1/1→1/3 (v/v)) to give the title compound as a brown solid (1.50 mg, yield 7.5%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (1.0 mL)
  3. temperatureunder cooling with ice
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl hexane/acetate=4/1→1/1→1/3 (v/v))

Sources & evidence

ORD record
ord-5996f67b8019493f84368f995b55ba16
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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