Pyridine → HCID 44358275, compound

HRID 322106Notes

Reaction equation

HRID 322106 reaction equation
[C:1](Cl)(Cl)=[O:2].[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N:14]3[CH2:18][CH2:17][C@@H:16]([NH2:19])[CH2:15]3)[C:8]=2[CH2:7][CH2:6]1.[N:20]1[CH:25]=[CH:24][CH:23]=CC=1.C1(N)CC1>C1COCC1>[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N:14]3[CH2:18][CH2:17][C@@H:16]([NH:19][C:1]([NH:20][CH:25]4[CH2:23][CH2:24]4)=[O:2])[CH2:15]3)[C:8]=2[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 69828CyclopropylamineHCID 69830104HCID 69830104, compound

Product 1

HCID 44358275HCID 44358275, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosgene (1 mL, 20% in toluene) was added to a solution of (R)-N-(2,3-dihydrobenzofuran-4-yl)-3-(amino)pyrrolidine (102 mg) and pyridine (79 mg) in THF (5.6 mL) at 0° C. After stirring for 20 min, cyclopropylamine (228 mg) was added to the reaction and the reaction mixture was allowed to warm to room temperature. After stirring for 2 h, the reaction was quenched with water and THF was removed. The residue was purified by flash chromatography over silica gel (elution with 5% methanol in ethyl acetate) to give 110 mg (77%) of the desired product as solid.

Workup

  1. stirringAfter stirring for 2 h
  2. customthe reaction was quenched with water and THF
  3. customwas removed
  4. customThe residue was purified by flash chromatography over silica gel (elution with 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-d5ad3dc7cdd648918b12035b8301dbed
Source dataset
uspto-grants-2001_04
Patent number
US06211225B1

Reaction notes

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