Triethylamine → HCID 10180014, compound

HRID 1071569Notes

Reaction equation

HRID 1071569 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3]1.Cl.C[NH:33][O:34][CH3:35].C(N(CC)CC)C>ClCCl>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[C:13]([C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:33][O:34][CH3:35])=[O:27])=[CH:24][CH:23]=4)[NH:14][C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 22394525HCID 22394525, compound

Product 1

HCID 10180014HCID 10180014, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzoyl chloride hydrochloride (100 mg; 0.23 mmol) was suspended in dichloromethane (10 ml), N,O-dimethyl hydroxylamine hydrochloride (38 mg; 0.45 mmol) added followed by triethylamine (0.16 ml; 1.1 mmol). The resulting mixture was stirred at ambient temperature for 18 h. The mixture was evaporated to dryness under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure. The title compound (4 mg; 4%) was obtained by high performance liquid chromatography. 1H NMR (250 MHz; CD3OD) δ: 3.74 (3H, s), 6.00 (2H, s), 6.94 (1H, d,), 7.04-7.08 (2H, m), 7.50-7.70 (2H, m), 7.85 (2H, d), 8.00-8.20 (3H, m), 8.59 (1H, d); m/z (ESMS): 415.1 [M+H]⊕.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3171a62b24424bbdbc1dd8c764d29e20
Source dataset
uspto-grants-2005_06
Patent number
US06906089B2

Reaction notes

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