Acetyl chloride → HCID 57814721, compound

HRID 521610Notes

Reaction equation

HRID 521610 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:8][C:7]=1[C:23]1[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl>[C:36]([NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:8][C:7]=1[C:23]1[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67265457N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide hydrochloride

Product 1

HCID 57814721HCID 57814721, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-methoxybenzamide hydrochloride (30.0 mg, 74.5 μmol) and triethylamine (31.1 μL, 3.0 eq) were taken up in 2 mL of dichloromethane and stirred for 15 mins. To this was added acetyl chloride (6.35 μL, 1.2 eq) and the reaction was stirred at room temperature for 18 hrs. The solvents were evaporated under a stream of nitrogen and it was purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 54.3% yield. LCMS m/z (%)=409 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 1.97 (s, 3H), 3.49-3.56 (m, 2H), 3.85 (s, 3H), 3.88 (s, 3H), 4.09 (t, J=5.05 Hz, 2H), 6.36 (t, J=6.32 Hz, 1H), 6.39 (d, J=2.02 Hz, 1H), 7.02 (d, J=8.59 Hz, 1H), 7.09-7.13 (m, 1H), 7.36-7.45 (m, 2H), 7.61 (dd, J=9.09, 2.53 Hz, 1H), 7.69 (d, J=1.52 Hz, 1H), 7.75 (d, J=2.02 Hz, 2H), 7.85 (s, 1H).

Workup

  1. stirringthe reaction was stirred at room temperature for 18 hrs
  2. customThe solvents were evaporated under a stream of nitrogen and it
  3. customwas purified by HPLC
  4. customThe proper fractions were collected

Sources & evidence

ORD record
ord-0dbc5eac24674e50963f4f85107905c2
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

Loading…