Acetyl chloride → HCID 11952510, compound

HRID 1241482Notes

Reaction equation

HRID 1241482 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([N:15]1[C:21](=[O:22])[C:20]2[CH:23]=[C:24]([I:27])[CH:25]=[CH:26][C:19]=2[NH:18][C:17](=[O:28])[CH:16]1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH3:14].C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)Cl>[C:1]([NH:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]([N:15]1[C:21](=[O:22])[C:20]2[CH:23]=[C:24]([I:27])[CH:25]=[CH:26][C:19]=2[NH:18][C:17](=[O:28])[CH:16]1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[CH3:14])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11226830HCID 11226830, compound

Product 1

HCID 11952510HCID 11952510, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (15 μL, 0.212 mmol) was added at 0° C. under argon to a solution of 1,3-dihydro-4-[1-(2-amino-4-chlorophenyl)ethyl]-3-(4-chloropenyl)-7-iodo-1,4-benzodiazepine-2,5-dione (100 mg, 0.177 mmol), in tetrahydrofuran (5 mL) and chloroform (5 mL). Then, triethylamine (30 μL, 0.21 mmol) was added drop wise and the reaction mixture was allowed warm up to room temperature. After 30 minutes, the solution was concentrated under reduced pressure and the residue was petitioned between ethylacetate and 1N sodium bicarbonate. Organic layer was dried (Na2SO4), evaporated, and the residue was purified by column chromatography to give the title compound (49 mg, 45%) as a colorless powder: 1H NMR (400 MHz, CDCl3) δ 1.81 (d, J=6.8 Hz, 3H), 2.44 (s, 3H), 5.33 (s, 1H), 6.37 (q, J=6.8 Hz, 1H), 6.47 (d, J=8.4 Hz, 2H), 6.55 (d, J=8.4 Hz, 1H), 6.98 (d, J=8.4 Hz, 2H), 7.03 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.59 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 8.28 (br s, 1H), 8.54 (d, J=2.0 Hz, 1H), 9.94 (s, 1H). Mass spectrum (LCMS, ESI pos.): Calcd for C25H20Cl2IN3O3: 607; found: 608 (M+H)+.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dry with materialOrganic layer was dried (Na2SO4)
  3. customevaporated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1432aff4e2034b6da394bc9018d292bf
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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