Triethylamine → N-(4-(Diethylamino)phenyl)-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 1243129Notes

Reaction equation

HRID 1243129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2.S(O)(O)(=O)=O.[CH2:21]([N:23]([CH2:31][CH3:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1N)[CH3:22].CC[N:35](CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH2:21]([N:23]([CH2:31][CH3:32])[C:24]1[CH:29]=[CH:28][C:27]([NH:35][C:13]([CH:10]2[CH2:9][CH2:8][C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=3)[CH2:11]2)=[O:15])=[CH:26][CH:25]=1)[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36247098-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic AcidHCID 21940395N,N-diethylphenylene diamine sulfate

Product 1

HCID 11484968N-(4-(Diethylamino)phenyl)-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamideYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (206 mg, 1.0 mmol) in DMF (1.5 mL) was added N,N-diethylphenylene diamine sulfate (262 mg, 1.0 mmol), Et3N (606 mg, 6.0 mmol), and TBTU (321 mg, 1.0 mmol) at 0° C. After stirred overnight, ice chips and 20 mL ethyl acetate were added. Organic layer was washed with water (3×10 mL), dried over MgSO4, and then concentrated. Purification by column chromatography provided the titled compound (170 m g, 48%). 1H NMR (300 MHz, DMSO-D6) δ 9.59 (s, 1H), 7.39 (d, J=9.3 Hz, 2H), 7.08 (t, J=7.8 Hz, 1H), 6.75 (d, J=7.8 Hz, 1H), 6.70 (d, J=7.8 Hz, 1H), 6.61 (d, J=9.0 Hz, 2H), 3.76 (s, 3H), 3.29 (q, J=6.9 Hz, 4H), 2.91–2.56 (m, 5H), 2.00 (m, 1H), 1.69 (m, 1H), and 1.06 (t, J=6.9 Hz, 6H). MS (ESI) positive ion 353 (M+H)+; negative ion 351 (M−H)−.

Workup

  1. washOrganic layer was washed with water (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-4b3135d77be04fec87d42fab2b48ce59
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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