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Triethylamine → 5-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-pentanoic Acid Methyl Ester

HRID 220927
Notes
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Reaction equation

HRID 220927 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH3:18])=[O:4].[CH3:19][N:20]1[C:29]2[NH:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[NH:25][CH2:24][C:23]=2[CH:22]=[N:21]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([N:25]2[CH2:24][C:23]3[CH:22]=[N:21][N:20]([CH3:19])[C:29]=3[NH:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]2=3)=[O:15])=[CH:11][C:10]=1[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 575553514-(4-Methoxycarbonyl-butyl)-3-methyl-benzoic AcidHCID 1357419771-Methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine

Product 1

HCID 1361283645-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-pentanoic Acid Methyl EsterYield 46%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

WSCD (822 mg, 4.3 mmol) and DMAP (273 mg, 2.2 mmol) were added to a solution of 4-(4-methoxycarbonyl-butyl)-3-methyl-benzoic acid from Example E31 (571 mg, 2.3 mmol) and 3-methyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene from Example E11 (424 mg, 2.1 mmol) in dichloromethane (50 ml) and triethylamine (0.6 ml, 4.3 mmol). The mixture was heated at reflux for 72 h, diluted with dichloromethane, washed with 0.3M KHSO4, saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc to 5% triethyamine: 95% EtOAc) to yield the title compound (424 mg, 46%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 72 h
  3. washwashed with 0.3M KHSO4, saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc to 5% triethyamine: 95% EtOAc)

Sources & evidence

ORD record
ord-06ad42413b314af7a436b20695891ed7
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes