Triethylamine → HCID 90310966, compound

HRID 927208Notes

Reaction equation

HRID 927208 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=1[S:35][CH3:36])[C:11]1[C:12](=[O:27])[CH2:13][CH2:14][C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1.[C:37](N1C=CN=C1)(N1C=CN=C1)=[O:38]>C(#N)C>[Br:34][C:31]1[CH:32]=[CH:33][C:28]([CH:10]2[NH:9][C:37](=[O:38])[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=3)[C:15]3[CH2:14][CH2:13][C:12](=[O:27])[C:11]2=3)=[C:29]([S:35][CH3:36])[CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90311039HCID 90311039, compound2×

Product 1

HCID 90310966HCID 90310966, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (250 μL, 1.81 mmol) is added to a mixture of 2-(amino(4-bromo-2-(methyl-thio)phenyl)methyl)-3-(3-(trifluoromethyl)phenyl amino)cyclopent-2-enone hydrochloride (intermediate 20.5, 4.08 g, 7.23 mmol based on 90% purity) and 1,1′-carbonyldiimidazole (1.46 g, 9.04 mmol) in acetonitrile (54 mL), and the mixture is stirred at room temperature for 1 h. All volatiles are removed under reduced pressure, and the residue is treated with water. The precipitate is filtered and purified by flash chromatography on silica (gradient dichloromethane to dichloromethane/methanol 95:5). Yield: 3.04 g; ESI mass spectrum: [(79Br)-M+H]+=497, [(81Br)-M+H]+=499; Retention time HPLC: 0.65 min (X011_S03).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. additionthe residue is treated with water
  3. filtrationThe precipitate is filtered
  4. custompurified by flash chromatography on silica (gradient dichloromethane to dichloromethane/methanol 95:5)
  5. custom0.65 min (X011_S03)

Sources & evidence

ORD record
ord-8e32127f308541edbad8d2f9f28ea62b
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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