Triethylamine → HCID 70975393, compound

HRID 1190824Notes

Reaction equation

HRID 1190824 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:20]([O:24][C:25](=[O:46])[NH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]2[C:38]([NH2:39])=[C:37]([NH:40][CH3:41])[N:36]=[C:35](C(OC)=O)[CH:34]=2)[CH2:28]1)([CH3:23])([CH3:22])[CH3:21].[C:47](=O)([O-])[O-:48].[Na+].[Na+]>O1CCCC1.ClCCl.O>[C:20]([O:24][C:25]([NH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]2[CH:34]=[C:35]([C:5]([O:6][CH3:7])=[O:11])[N:36]=[C:37]3[N:40]([CH3:41])[C:47](=[O:48])[NH:39][C:38]=23)[CH2:28]1)=[O:46])([CH3:21])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 94429TriphosgeneHCID 70975608HCID 70975608, compound

Product 1

HCID 70975393HCID 70975393, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a dry reaction bottle, 8.32 g triphosgene (28 mmol) and 7.8 mL triethylamine (56 mmol) were added and dissolved in 240 mL tetrahydrofuran. A solution of 5.31 g (R)-1-[2-methoxycarbonyl-5-amino-6-methylaminopyridin-4-yl]piperidine-3-carbamic acid tert-butyl ester (14 mmol) in tetrahydrofuran (80 mL) was added dropwise at −10° C. After addition, the reaction solution was adjusted to be neutral with saturated sodium carbonate solution. Water and dichloromethane were added to the reaction solution. The reaction solution was extracted with dichloromethane. The organic phase was combined, washed with saturated brine, dried with anhydrous sodium sulfate, evaporated to remove dichloromethane, washed with ethyl acetate, filtrated, and dried to afford 4.1 g titled product as white solid, with a yield of 72.3%.

Workup

  1. additionwere added
  2. additionAfter addition
  3. extractionThe reaction solution was extracted with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. customto remove dichloromethane
  8. washwashed with ethyl acetate
  9. filtrationfiltrated
  10. customdried

Sources & evidence

ORD record
ord-3acdec0e2f1b4822adf2d68e70fa1817
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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