Triethylamine → HCID 67159457, compound

HRID 1503869Notes

Reaction equation

HRID 1503869 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.O.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 2880572486-69-3HCID 178526939HCID 178526939, compound

Product 1

HCID 67159457HCID 67159457, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3-methoxybenzoic acid (167 mg, 1 mmol) in dichloromethane (20 mL) at 0° C. was added pyrrolidine (71 mg, 1 mmol), hydroxybenzotriazole monohydrate (270 mg, 2 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (384 mg, 2 mmol) and triethylamine (0.5 mL, 3 mmol). After stirring for 2 hours, the mixture was diluted with water and extracted with dichloromethane. The organic phase was concentrated and the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 5/1 petroleum ether/ethyl acetate to give the title compound. MS: 220 (M+H+).

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic phase was concentrated
  3. customthe residue was purified by flash chromatography on silica gel (200-300 mesh)
  4. washeluting with 5/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-09fc1eb909dc439fb105ce48f48c9720
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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