Aniline → HCID 86747052, compound

HRID 484466Notes

Reaction equation

HRID 484466 reaction equation
[C:1]([CH2:4][C@@H:5]1[C:14]2[C:9](=[CH:10][C:11]([Cl:16])=[CH:12][C:13]=2[Cl:15])[NH:8][C@@H:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6]1)([OH:3])=O.O[C:25]1[C:33]2N=N[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1.NC1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>C1COCC1.C(N(CC)CC)C>[C:29]1([NH:30][C:1]([CH2:4][C@@H:5]2[C:14]3[C:9](=[CH:10][C:11]([Cl:16])=[CH:12][C:13]=3[Cl:15])[NH:8][C@@H:7]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:6]2)=[O:3])[CH:33]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86747053HCID 86747053, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86747052HCID 86747052, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Trans-4-carboxymethyl-2-tertiarybutyloxycarbonyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.25 g, 0.000696M) was dissolved in dry THF with dry triethylamine (0.29 ml, 3 molar equivalents), hydroxybenzotriazole (0.141 g, 1.5 molar equivalents), aniline (0.0925 ml, 1.5 molar equivalents) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.2 g, 1.5 molar equivalents) and the reaction mixture was stirred at room temperature for 14 h. The solvents were removed in vacuo and the residue was dissolved in ethyl acetate (100 ml) and washed successively with 0.5 normal citric acid solution (3×50 ml), saturated sodium hydrogen carbonate solution (3×50 ml) and brine (1×50 ml), dried (Na2SO4), filtered and evaporated under vacuum. The residue obtained was purified by chromatography on silica gel using 10% ethyl acetate in hexane as eluent to give the title compound (0.14 g) as a colourless oil; δ (250 MHz, DMSO) 1.48 (9H, s, (CH3)3C), 1.69 (1H, ddd, J=13.0, 12.4 and 4.0 Hz, CHACHBHCCHD), 2.47 (2H, m, CHACHBHCCHDCHEHFCONHPh), 2.73 (1H, dd, J=16.5 and 2.5 Hz, CHACHBHCCHDCHEHFCONHPh), 3.73 (1H, m, CHACHBHCCHDCHEHFCONHPh), 3.98 (1H, dd, J=12.4 and 3.3 Hz, CHACHBHCCHDCHEHFCONHPh), 4.72 (1H, br, s, ArNHCHA), 6.50 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.15 (2H, m, p-proton and PhNH), 7.33 (2H, t, J=7.5 Hz, m protons), 7.50 (2H, d, J=7.5 Hz, o protons); m/e (FAB) 379 (M+1).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed successively with 0.5 normal citric acid solution (3×50 ml), saturated sodium hydrogen carbonate solution (3×50 ml) and brine (1×50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue obtained
  8. customwas purified by chromatography on silica gel using 10% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-a53ad761c3364d84a248892fd81ea701
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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