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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
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HRID 220913 반응식
[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
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참가 물질

6

반응물 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

생성물 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)-methanone수율 4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매
HCID 8471Triethylamine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f70706eb763f424ea2b1d5fe3172f524
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202858B2

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