Triethylamine → HCID 58714287, compound

HRID 1241483Notes

Reaction equation

HRID 1241483 reaction equation
[C:1]([C:4]1[CH:32]=[CH:31][C:7]2[NH:8][C:9](=[O:30])[C@H:10]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:11]([C@@H:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH3:15])[C:12](=[O:13])[C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[NH2:34][OH:35].C(N(CC)CC)C.C(Cl)Cl.CO>CCO>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:10]2[C:9](=[O:30])[NH:8][C:7]3[CH:31]=[CH:32][C:4]([C:1](=[N:34][OH:35])[CH3:2])=[CH:5][C:6]=3[C:12](=[O:13])[N:11]2[C@@H:14]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH3:15])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21060019HCID 21060019, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 58714287HCID 58714287, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-Acetyl-3-(S)-(4-chloro-phenyl)-4-[1-(R)-(4-chloro-phenyl)-ethyl]-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (50 mg, 0.11 mmol), hydroxylamine hydrochloride salt (22 mg, 0.33 mmol), triethylamine (0.074 mL, 0.55 mmol) in EtOH (0.5 mL) was heated to 80° C. After 2 h reaction solution was applied to a prep tlc plate (Analtech Silica Gel GF, 20×20 cm, 2000 microns) and developed using methylene chloride/MeOH 10:1. Desired bands were scraped off, extracted with MeOH, filtered and concentrated to give the title compound (2.4 mg). 1H NMR (400 MHz, DMSO-d6) δ 7.82–7.83 (m, 1H), 7.47–7.51 (m, 3H), 7.32 (s, 3H), 7.26–7.30 (m, 2H), 6.80–6.84 (m, 2H), 6.66–6.70 (d, J=8.4 Hz, 2H), 6.52–6.55 (d, J=8.6 Hz, 2H), 6.36–6.42 (m, 2H), 5.17 (s, 1H), 1.67–1.71 (d, J=7.3 Hz, 3H). Mass spectrum (LCMS, ESI pos.): Calcd for C25H21Cl2N3O3: 481.1; found 482.1 (M+H).

Workup

  1. customAfter 2 h reaction solution
  2. extractionextracted with MeOH
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da4b5bac9ff04112a69c18d7a3c6859a
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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