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Triethylamine → 4-(1-Benzyl-piperidin-4-yl)-1-(5-isopropyl-2,4-bismethoxymethoxy-benzoyl) thiosemicarbazide

HRID 1947186
Notes
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Reaction equation

HRID 1947186 reaction equation
C(N(CC)CC)C.[C:8](Cl)(Cl)=[S:9].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.[CH:26]([C:29]1[C:30]([O:43][CH2:44][O:45][CH3:46])=[CH:31][C:32]([O:39][CH2:40][O:41][CH3:42])=[C:33]([CH:38]=1)[C:34]([NH:36][NH2:37])=[O:35])([CH3:28])[CH3:27]>O1CCCC1>[CH2:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:8](=[S:9])[NH:37][NH:36][C:34](=[O:35])[C:33]2[CH:38]=[C:29]([CH:26]([CH3:28])[CH3:27])[C:30]([O:43][CH2:44][O:45][CH3:46])=[CH:31][C:32]=2[O:39][CH2:40][O:41][CH3:42])[CH2:14][CH2:15]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 4158521-Benzyl-4-piperidylamineHCID 598298425-Isopropyl-2,4-bis-methoxymethoxy-benzoic acid hydrazide

Product 1

HCID 598298694-(1-Benzyl-piperidin-4-yl)-1-(5-isopropyl-2,4-bismethoxymethoxy-benzoyl) thiosemicarbazide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Tetrahydrofuran (5 mL), triethylamine (0.086 mL, 1.25 mmol), thiophosgene (0.042 mL, 0.55 mmol) and 4-amino-1-benzyl-piperidine (0.112 mL, 0.55 mmol) were placed in a 10 mL eggplant shaped flask and stirred at room temperature for 2 hours, and then 5-isopropyl-2,4-bis-methoxymethoxy-benzoic acid hydrazide (IM4-a, 149 mg, 0.5 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After completing the reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was subjected to the next reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 hours
  2. customthe reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas subjected to the next reaction without further purification

Sources & evidence

ORD record
ord-fc75e59c4b6043248bc09bb126f8ee7e
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399464B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes