Triethylamine → HCID 70975548, compound

HRID 1190818Notes

Reaction equation

HRID 1190818 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:20]([O:24][C:25](=[O:53])[NH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]2[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]([NH:40][CH2:41][C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=3[O:50][CH3:51])[C:34]=2[NH2:52])[CH2:28]1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:20]([O:24][C:25](=[O:53])[NH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]2[CH:38]=[C:37]([CH3:39])[N:36]=[C:35]3[N:40]([CH2:41][C:42]4[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=4[O:50][CH3:51])[C:2](=[O:4])[NH:52][C:34]=23)[CH2:28]1)([CH3:22])([CH3:21])[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 94429TriphosgeneHCID 70975487HCID 70975487, compound

Product 1

HCID 70975548HCID 70975548, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

1.42 g triphosgene (4.78 mmol) was dissolved in 10 mL dichloromethane, and cooled to −10° C. 1.77 mL triethylamine (12.72 mmol) was added. A solution of 1.5 g (R)-1-[2-(2,4-dimethoxybenzyl)amino-6-methyl-3-aminopyridin-4-yl]piperidine-3-carbamic acid tert-butyl ester (3.18 mmol) in dichloromethane (20 mL) was slowly added dropwise at −10° C. After they were completely reacted, the reaction solution was adjusted to be basic by adding saturated sodium carbonate solution, and extracted twice with dichloromethane. The combined organic phase was washed with brine, dried with anhydrous sodium sulfate, and evaporated to dryness. The resultant crude product was recrystallized with dichloromethane and ethyl acetate to afford 1.03 g titled product with a yield of 65.2%.

Workup

  1. customAfter they were completely reacted
  2. extractionextracted twice with dichloromethane
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe resultant crude product was recrystallized with dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-7c02704cd2304c80af364f21c31a9c09
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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