Triethylamine → HCID 67970734, compound

HRID 889544Notes

Reaction equation

HRID 889544 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:19])=[C:9]([CH:18]=1)[C:10]([NH:12][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)=[O:11].C(N(CC)CC)C.[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29]>C1COCC1>[Cl:19][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][NH:3][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[CH:18][C:9]=1[C:10]([NH:12][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 67970680HCID 67970680, compound

Product 1

HCID 67970734HCID 67970734, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-(aminomethyl)-2-chloro-N-(1H-imidazol-2-yl)benzamide dihydrochloride (50 mg, 0.154 mmol, 1.0 equiv) in THF (0.77 mL), add triethylamine (80 μL, 0.57 mmol, 3.7 equiv) and isobutyryl chloride (16.3 μL, 0.154 mmol, 1.0 equiv), and stir the reaction mixture for 1 h at room temperature. Concentrate the reaction mixture under reduced pressure, triturate the crude solids with a mixture of water (10 mL), hexanes (10 mL), and diethyl ether (10 mL), isolate the white solid by filtration and dry in a 40° C. vacuum oven to give the title compound (19 mg, 38% yield): 1H NMR (DMSO-d6, 400 MHz): δ 11.74 (br s, 2H), 8.30 (t, 1H, J=6.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.36 (d, 1H, J=2.0 Hz), 7.26 (dd, 1H, J=8.0, 2.0 Hz), 6.73 (br s, 2H), 4.22 (d, 2H, J=5.9 Hz), 2.37 (septet, 1H, J=6.6 Hz), 0.97 (d, 6H, J=6.8 Hz). MS (m/z) (35Cl/37Cl) 321/323 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. customtriturate the crude solids
  3. additionwith a mixture of water (10 mL), hexanes (10 mL), and diethyl ether (10 mL)
  4. customisolate the white solid
  5. filtrationby filtration
  6. customdry in a 40° C. vacuum oven

Sources & evidence

ORD record
ord-34debfd94d494ba58a79a344345a08fe
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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