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4-Aminopyridine → 4-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methyl-n-(4-pyridinyl)benzamide

HRID 393295
Notes
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Reaction equation

HRID 393295 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]=3[CH3:26])=[CH:13][C:8]=2[C:7](=[O:27])[N:6]([CH3:28])[C:5]2[CH:29]=[CH:30][CH:31]=[N:32][C:4]1=2)[CH3:2].[NH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:14][CH2:15][O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([NH:33][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[O:22])=[CH:19][C:18]=3[CH3:26])=[CH:13][C:8]=2[C:7](=[O:27])[N:6]([CH3:28])[C:5]2[CH:29]=[CH:30][CH:31]=[N:32][C:4]1=2)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 226488664-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methyl benzoyl chloride

Product 1

HCID 226488574-[2-(11-Ethyl-6,11-dihydro-5-methyl-6-oxo-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-8-yl)ethoxy]-3-methyl-n-(4-pyridinyl)benzamideYield 103.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[2-(11-ethyl-6,11-dihydro-5-methyl-6-oxo-5H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-8-yl)ethoxy]-3-methylbenzoyl chloride (47.4 mg, 0.11 mmol), 4-aminopyridine (9.88 mg, 0.11 mmol) and Et3N (15.3 μL, 0.11 mmol) in CH2Cl2 (4 mL) was stirred at 25° C. for 5 h. The reaction mixture was diluted with EtOAc and the resulting solution was successively washed with aqueous saturated NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (58 mg, 100% yield) as a colorless oil.

Workup

  1. washthe resulting solution was successively washed with aqueous saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1669001f7aa468c86989efeb925e8cb
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806265B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes