Diisopropylethylamine → HCID 57550367, compound

HRID 544961Notes

Reaction equation

HRID 544961 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(C(C)C)CC)(C)C.[CH2:25]([O:32][CH2:33][C:34](Cl)=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH2:25]([O:32][CH2:33][C:34]([N:12]1[CH2:13][CH2:14][CH2:15][N:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:10][CH2:11]1)=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 177085Benzyloxyacetyl chlorideHCID 575503481-(2,4-Dichlorophenyl)-1,4-diazepane

Product 1

HCID 57550367HCID 57550367, compoundYield 452%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2,4-dichloro-phenyl)-[1,4]diazepane (0.11 g, 0.45 mmol) in dichloromethane (5 mL) was added diisopropyl-ethylamine (0.082 mL, 0.47 mmol) and benzyloxyacetyl chloride (0.086 g, 0.47 mmol). The solution was stirred at room temperature for 1 h. The residue was chromatographed on silica gel using dichloromethane/ethyl acetate from 100% to 95% dichloromethane in a gradient fashion, to obtain the title compound as a gum (0.80 g, 46%). 1H NMR (300 MHz, CDCl3): δ 7.33 (m, 6H), 7.14 (m, 1H), 6.96 (m. 1H), 4.64 (m, 2H), 4.21 (m, 2H), 3.79 (m, 2H), 3.65 (m, 2H), 3.19 (m, 4H), 2.04 (m, 2H).

Workup

  1. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-42ff27705af64b5eb0ad1d7f78d48a41
Source dataset
uspto-grants-2011_05
Patent number
US07935703B2

Reaction notes

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