Propylamine → HCID 70170461, compound

HRID 2171206Notes

Reaction equation

HRID 2171206 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[O:23][CH2:22]4)[C:7]=2[O:8][CH2:9][C:10]([OH:12])=O)[CH2:3][CH2:2]1.CCN=C=[N:33][CH2:34][CH2:35][CH2:36]N(C)C.Cl.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C(N)CC>ClCCl.O>[CH:1]1([CH2:4][O:5][C:6]2[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[O:23][CH2:22]4)[C:7]=2[O:8][CH2:9][C:10]([NH:33][CH2:34][CH2:35][CH3:36])=[O:12])[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 7852PropylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71279403HCID 71279403, compound

Product 1

HCID 70170461HCID 70170461, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(2-(cyclopropylmethoxy)-3-methoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)acetic acid (200 mg, 0.519 mmol) in dichloromethane (20 mL) was added EDCI.HCl (150 mg, 0.779 mmol), triethylamine (156 mg, 1.55 mmol), HOBt (158 mg, 1.038 mmol) and propylamine (91 mg, 1.553 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 5-40% ethyl acetate in pet ether) afforded the title compound as a solid (30 mg, 14%).

Workup

  1. customthe resultant reaction mixture
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined dichloromethane layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by flash column chromatography (silica gel, 5-40% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-e73c08ce73144f299b5063710ca20c2f
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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