1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

HRID 1935654Notes

Reaction equation

HRID 1935654 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:19](O)=[O:20])=[CH:7][C:8]2[C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]=2[CH:14]=1.[F:22][C:23]1[CH:32]=[C:31]([NH2:33])[CH:30]=[C:29]([F:34])[C:24]=1[C:25]([O:27][CH3:28])=[O:26].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:22][C:23]1[CH:32]=[C:31]([NH:33][C:19]([C:6]2[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:14][C:13]3[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]([CH3:18])([CH3:17])[C:8]=3[CH:7]=2)=[O:20])[CH:30]=[C:29]([F:34])[C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 158405323-(Methoxymethoxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 23001755Methyl 4-amino-2,6-difluorobenzoate

Product 1

HCID 22465055Methyl 2,6-difluoro-4-[(3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxymethoxy-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (Compound K, as described in U.S. Pat. No. 5,856,490, 112mg, 0.38 mmol) in 6 ml of anhydrous methylene chloride was added 4-(dimethylamino)pyridine (DMAP, 100 mg, 0.46mmol), methyl 2,6-difluoro-4-aminobenzoate (Compound H1, as described in U.S. Pat. No. 5,856,490, 77mg, 0.38mmol ) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 110 mg, 0.57 mmol). The reaction mixture was stirred at room temperature for overnight then concentrated to dryness. The residue was purified by column chromatography with ethyl acetate: hexane (1:9) to yield the title compound as a clear oil.

Workup

  1. concentrationthen concentrated to dryness
  2. customThe residue was purified by column chromatography with ethyl acetate: hexane (1:9)

Sources & evidence

ORD record
ord-da1dd56b9f354d9ca2f8683bc6214c71
Source dataset
uspto-grants-2002_05
Patent number
US06387950B2

Reaction notes

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