Triethylamine → HCID 23511893, compound

HRID 354314Notes

Reaction equation

HRID 354314 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[S:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.[C:36]1([CH3:45])[C:37]([N:42]=[C:43]=[O:44])=[CH:38][CH:39]=[CH:40][CH:41]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:43]([NH:42][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:45])=[O:44])=[CH:26][CH:27]=2)[S:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 23512000HCID 23512000, compound

Product 1

HCID 23511893HCID 23511893, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methoxy-4-[2-(4-aminobenzyl)-4-thiazolyl]methoxybenzoate (87.8 mg, 0.220 mmol) in THF (2.0 mL) was added triethylamine (30.5 ul, 0.220 mmol) and o-tolyl isocyanate (30 μl), and the reaction mixture was stirred at room temp for 21 hr. The reaction mixture was poured into ice-water and the resulting precipitates filtered off. The filtrate was extracted with CHCl3, washed with H2O, and brine. The extract was dried over Na2SO4. The solvent was removed under a reduced pressure to afford 110.4 mg (94%) ethyl 3-methoxy-4-[2-[4-[N′-(2-methylphenyl)ureido]benzyl]-4-thiazolyl]methoxybenzoate as a pale yellow crystalline powder. 1H-NMR (400 MHz, CDCl3) δ1.38 (t, J=7.3 Hz, 3H), 2.28 (s, 3H), 3.92 (s, 3H), 4.28 (s, 2H), 4.35 (q, J=7.3 Hz, 2H), 5.29 (s, 2H), 6.20 (s, 1H), 6.47 (s, 1H), 6.97 (d, J=8.8 Hz, 1H), 7.20 (s, 1H), 7.24 (s, 2H), 7.27 (s, 2H), 7.33 (d, J=8.3 Hz, 2H), 7.49 (d, J=7.3 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.63 (dd, J=2.0, 8.3 Hz, 1H); MS (FAB) m/z 532 M++1).

Workup

  1. customthe resulting precipitates
  2. filtrationfiltered off
  3. extractionThe filtrate was extracted with CHCl3
  4. washwashed with H2O, and brine
  5. dry with materialThe extract was dried over Na2SO4
  6. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-5a9d3f92c35b472a8300acdcc7c07240
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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