HCID 59676073, compound → HCID 59676116, compound

HRID 624498Notes

Reaction equation

HRID 624498 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)[C:18]3[C:17]4[CH:36]=[CH:37][CH:38]=[CH:39][C:16]=4[S:15][CH2:14][CH2:13][C:12]=3[C:11]=2[CH:40]=1)(C)(C)C>CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>[N:30]1([CH2:29][CH2:28][O:27][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][N:19]3[C:18]4[C:17]5[CH:36]=[CH:37][CH:38]=[CH:39][C:16]=5[S:15][CH2:14][CH2:13][C:12]=4[C:11]4[CH:40]=[C:7]([OH:6])[CH:8]=[CH:9][C:10]3=4)=[CH:22][CH:23]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

4

Reactant 1

HCID 59676073HCID 59676073, compound

Product 1

HCID 59676116HCID 59676116, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

9-(tert-Butyl-dimethyl-silanyloxy)-12-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-6,7-dihydro-12H-5-thia-12-aza-dibenzo[a,e]azulene (130 mg, 0.222 mmol) in 5 mL 1.0 N TBAF in THF solution was stirred for 30 min at room temperature. The reaction was worked up by CH2Cl2 extraction three times from water. The combined organic layer was dried and concentrated and purified by column using 4:1 CH2Cl2 and methanol solution to yield the title compound as a brown solid.

Workup

  1. extractionThe reaction was worked up by CH2Cl2 extraction three times from water
  2. customThe combined organic layer was dried
  3. concentrationconcentrated
  4. custompurified by column

Sources & evidence

ORD record
ord-1e159d8b88ac435b9fe0c0360d25c3a2
Source dataset
uspto-grants-2016_04
Patent number
US09303037B2

Reaction notes

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