Triethylamine → HCID 24888597, compound

HRID 521636Notes

Reaction equation

HRID 521636 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>ClCCl>[CH2:39]([O:38][C:36](=[O:37])[NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[C:22]1[N:26]([CH3:27])[N:25]=[CH:24][CH:23]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 46833678N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide

Product 1

HCID 24888597HCID 24888597, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl), phenyl)-3-methoxybenzamide (50 mg, 136 μmol) and triethylamine (0.038 mL, 0.27 mmol) in dichloromethane was added benzyl chloroformate (26 mg, 150 μmol), dropwise at room temperature. The mixture was stirred at room temperature overnight. The reaction was quenched with water, extracted with dichloromethane (3×20 mL) and dried over anhydrous MgSO4. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography. (EtOAc/Hexane=50-90%). {2-[4-(3-Methoxy-benzoylamino)-2-(2-methyl-2H-pyrazol-3-yl)-phenoxy]-ethyl}-carbamic acid benzyl ester was obtained as white solid in 37% yield. LCMS m/z (%)=501 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 3.5 (q, J=5.4 Hz, 2H), 3.7 (s, 3H), 3.9 (s, 3H), 4.0 (t, J=5.1 Hz, 2H), 4.9 (t, J=5.8 Hz, 1H), 5.1 (s, 2H), 6.3 (d, J=2.0 Hz, 1H), 7.0 (d, J=8.6 Hz, 1H), 7.1 (m, 1H), 7.3 (m, 5H), 7.4 (m, 1H), 7.5 (m, 2H), 7.7 (dd, J=8.8, 2.8 Hz, 1H), 7.8 (s, 1H).

Workup

  1. customdropwise at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-acc9399bbddf4a27a8a1af42586a0b8a
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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