Pyridine → HCID 69462682, compound

HRID 1297128Notes

Reaction equation

HRID 1297128 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[N:12](CC)[C:11](=[O:15])[CH:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])[N:9]=[C:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]=2[CH:30]=1.N1C=CC=CC=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([O:31][CH3:32])=[CH:5][C:6]2[NH:12][C:11](=[O:15])[CH:10]([C:16]3[CH:17]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][NH:23][C:39](=[O:41])[CH3:40])[N:9]=[C:8]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:7]=2[CH:30]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69463018HCID 69463018, compound

Product 1

HCID 69462682HCID 69462682, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40 mg (0.09 mmol) of 7,8-dimethoxy-1-ethyl-3-(2-aminobenzyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one IIca, add 18.4 mg (0.23 mmol) of pyridine in 4 ml of CH2Cl2, 11.5 mg (0.11 mmol) of acetic anhydride dropwise. Stir for 24 hours. Evaporate to dryness and purify by silica chromatography (AcOEt then AcOEt 5/CH2Cl2 4/EtOH 1). Yield: 70%. M: 144–145° C. 1H-NMR (CDCl3, 300 MHz): d 0.89–0.96 (m, 3H, CH3), 2.01 (s, 1H, COCH3), 3.36–3.45 (m, 2H, CHCH2), 3.61 (s, 3H, OCH3), 3.73–3.84 (m, 2H, CHCH2+1HNCH2), 3.91 (s, 3H, OCH3), 6.60 (s, 1H Ar), 7.07–7.61 (m, 10H Ar). Mass: (M+H)+=472.23.

Workup

  1. customEvaporate to dryness
  2. custompurify by silica chromatography (AcOEt
  3. custom144–145° C

Sources & evidence

ORD record
ord-1d97fc1e88b543e193b7b8df27830902
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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