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4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic Acid → (4-(2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy)-3-methyl-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone

HRID 220913
Notes
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Reaction equation

HRID 220913 reaction equation
[CH3:1][N:2]1[C:11]2[NH:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[NH:7][CH2:6][C:5]=2[CH:4]=[N:3]1.[CH3:16][C:17]([CH3:40])([CH3:39])[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][O:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][C:30]=2[CH3:38])[CH2:22][CH2:21]1>CN(C1C=CN=CC=1)C.ClCCl.C(N(CC)CC)C>[CH3:16][C:17]([CH3:40])([CH3:39])[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][O:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([N:7]3[CH2:6][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:11]=4[NH:10][C:9]4[CH:12]=[CH:13][CH:14]=[CH:15][C:8]3=4)=[O:34])=[CH:31][C:30]=2[CH3:38])[CH2:22][CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 575552124-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic AcidHCID 1357419771-Methyl-1,4,5,10-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepine

Product 1

HCID 135446062(4-(2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-ethoxy)-3-methyl-phenyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanoneYield 4%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8471TriethylamineSolvent

Procedure

WSCD (58 mg, 0.30 mmol) and DMAP (20 mg, 0.15 mmol) were added to a solution of 3-methyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene from Example E11 (37 mg, 0.20 mmol) and 4-{2-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-ethoxy}-3-methyl-benzoic acid from Example E40 (53 mg, 0.15 mmol) in dichloromethane (5 ml) and triethylamine (to pH9). The mixture was heated at re-flux for 2 days then concentrated in vacuo. The residue was dissolved in EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% chloroform) to give an off-white solid identified as the title compound (3.5 mg, 4%).

Workup

  1. temperatureThe mixture was heated at re-flux for 2 days
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAC
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% chloroform)
  8. customto give an off-white solid

Sources & evidence

ORD record
ord-f70706eb763f424ea2b1d5fe3172f524
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