Chloroform → Ethyl Acetate

HRID 433907Notes

Reaction equation

HRID 433907 reaction equation
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[N:13]1([C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]1.[NH2:30][C@H:31]1[CH2:36][C:35]2[C:37]([N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)=[CH:38][CH:39]=[CH:40][C:34]=2[O:33][CH2:32]1.C(Cl)(Cl)Cl>CN(C)C=O.C(O)C>[C:25]([O:27][CH2:11][CH3:12])(=[O:26])[CH3:24].[CH3:47][N:44]1[CH2:45][CH2:46][N:41]([C:37]2[C:35]3[CH2:36][C@H:31]([NH:30][C:25](=[O:27])[C:24]4[CH:23]=[CH:22][C:21]([N:13]5[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]5)=[CH:29][CH:28]=4)[CH2:32][O:33][C:34]=3[CH:40]=[CH:39][CH:38]=2)[CH2:42][CH2:43]1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 682631,1'-CarbonyldiimidazoleHCID 11139461(S)-3-amino-5-(4-methylpiperazin-1-yl)-1,4-dihydro-2H-1-benzopyranHCID 220640304-(5-Oxo-1,4-diazepan-1-yl)benzoic acid

Product 2

HCID 8857Ethyl AcetateYield 204.2%HCID 22896527HCID 22896527, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,1′-carbonyldiimidazole (151 mg, 0.934 mmol) and 4-(hexahydro-1,4-diazepin-5-on-1-yl)benzoic acid (219 mg, 0.934 mmol) in anhydrous N,N-dimethylformamide (7 mL) was stirred at 75° C. for 55 min. The mixture was allowed to cool, and a solution of (S)-3-amino-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (210 mg, 0.85 mmol) in N,N-dimethylformamide (3.5 mL) was added. The reaction mixture was stirred at room temperature for 14 days. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica (eluent: chloroform/ethanol, 90:10+1% conc. NH3). The product was crystallized from a mixture of chloroform, ethanol, and ethyl acetate affording 84 mg (21% yield) of the title compound as white crystals: mp 244-247° C. (decomposes); [α]21D−148° (c 0.50, chloroform); TSPMS (70 eV) m/z 464 (M+1).

Workup

  1. temperatureto cool
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica (eluent: chloroform/ethanol, 90:10+1% conc. NH3)

Sources & evidence

ORD record
ord-051da950ade7454bbb99414e8201f9d6
Source dataset
uspto-grants-2003_12
Patent number
US06670359B2

Reaction notes

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