4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acid → HCID 11751078, compound

HRID 2076425Notes

Reaction equation

HRID 2076425 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.F[P-](F)(F)(F)(F)F.[N:34]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=N1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>CN(C=O)C.CCOC(C)=O>[NH2:34][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[NH:36][C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:25][CH:24]=1)=[O:22]

Participants

7

Reactant 4

HCID 21264-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acidHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 11751078HCID 11751078, compoundYield 4.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid 4 (151 mg) in DMF 2 mL was added BOP (0.266 g), triethylamine (0.238 mL, 0.60 mmol) and phenylenediamine (0.093 g, 0.86 mmol). The reaction mixture was stirred 1 h at RT and diluted in EtOAc (25 mL), washed with NaH2PO4 (1M, 2×25 mL), brine (1M, 2×25 mL), NaHCO3 (1M, 2×25 mL), brine (1M, 2×25 mL), dried over Na2SO4, filtered and concentrated to give an oil that was purified using silica gel chromatography with 40% [v/v] EtOAc in cyclohexane to give N-(4-(2-aminophenylcarbamoyl)phenyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide EHT 1800 (8 mg, 4% yield) as a white solid.

Workup

  1. washwashed with NaH2PO4 (1M, 2×25 mL), brine (1M, 2×25 mL), NaHCO3 (1M, 2×25 mL), brine (1M, 2×25 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oil that
  6. customwas purified

Sources & evidence

ORD record
ord-a6567c8f44b34d709d2eccf28a491d77
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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