Dichloromethane → HCID 14208259, compound

HRID 1084552Notes

Reaction equation

HRID 1084552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:19])[CH:10]([NH2:20])[N:9]=1.[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.C(N(CC)CC)C.[CH3:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].C([O:47][CH2:48]C)(=O)C.C(Cl)[Cl:51]>CN(C)C1C=CN=CC=1>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:9][CH:10]([NH:20][C:48]([C:40]3[CH:39]=[CH:38][C:43]([Cl:51])=[CH:42][CH:41]=3)=[O:47])[C:11]2=[O:19])=[O:27])=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 156371501,3-dihydro-5-(2-fluorophenyl)-3-amino-2H-1,4-benzodiazepin-2-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 14208259HCID 14208259, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 1,3-dihydro-5-(2-fluorophenyl)-3-amino-2H-1,4-benzodiazepin-2-one (400 mg, 1.49 mmole) in 25 ml of methylene chloride was added p-chlorobenzoyl chloride (380 μl, 3.0 mmole). Triethylamine was added to bring the pH of the reaction mixture to approximately 6 (moist pH paper) followed by 4-dimethylamino pyridine (183 mg, 1.5 mmole). After stirring at room temperature overnight the reaction mixture was diluted with methylene chloride to 200 ml and washed in succession with 10% citric acid solution (3×50 ml), saturated sodium bicarbonate solution, and brine. The organic extracts were dried (MgSO4) and concentrated to give 890 mg of crude product. Silica gel chromatography (hexane-ethyl acetate, 1:1 v/v) afforded the analytical product: m.p. 190°-191° C.

Workup

  1. washwashed in succession with 10% citric acid solution (3×50 ml), saturated sodium bicarbonate solution, and brine
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give 890 mg of crude product

Sources & evidence

ORD record
ord-27ea3c1fa65944c6b006cd37a504ca72
Source dataset
uspto-grants-1991_04
Patent number
US05004741

Reaction notes

Loading…