1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 22083286, compound

HRID 1376056Notes

Reaction equation

HRID 1376056 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18](=[O:33])[NH:19][CH:20]([C:29]([O:31]C)=[O:30])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18](=[O:33])[NH:19][CH:20]([C:29]([OH:31])=[O:30])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69216341HCID 69216341, compound

Product 1

HCID 22083286HCID 22083286, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-[2-(4-Chloro-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester: To a 0° C. solution of D-4-chlorophenylalanine methyl ester (23.8 g, 111.0 mmol), Boc-D-1,2,3,4-tetrahydroisoquinoline carboxylic acid (30.8 g,111.0) and 4-dimethylaminopyridine (75 mg, 0.61 mmol) in 200 mL of dichloromethane is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 30.8 g, 111.0 mmol) and the mixture stirred for 20 min. Remove ice bath and stir at room temperature for 4 hr. Wash 4 times with 200 mL each of water. The combined aqueous portions are extracted two times with 200 mL of dichloromethane. The combined organic portions are washed once with brine, dried (MgSO4), filtered and concentrated in vacuo. Chromatography (silica gel, 35% ethyl acetate/hexanes) of the residue affords 43.0 g (83%) of the title compound.

Workup

  1. stirringRemove ice bath and stir at room temperature for 4 hr
  2. washWash 4 times with 200 mL each of water
  3. extractionThe combined aqueous portions are extracted two times with 200 mL of dichloromethane
  4. washThe combined organic portions are washed once with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13d9afe26425476cb863b0470bd047e4
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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