US9290457, Example 1.5 → US9290457, Example 7

HRID 927015Notes

Reaction equation

HRID 927015 reaction equation
[C:1]([C:4]1[CH:5]([C:23]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][C:24]=2[C:25]([NH:27][CH2:28][C:29]#[CH:30])=[O:26])[N:6]([CH3:22])[C:7](=[O:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]>ClCCl.[Au](Cl)(Cl)Cl>[C:1]([C:4]1[CH:5]([C:23]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][C:24]=2[C:25]2[O:26][C:29]([CH3:30])=[CH:28][N:27]=2)[N:6]([CH3:22])[C:7](=[O:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 118691671US9290457, Example 1.52×

Product 1

HCID 118691676US9290457, Example 7

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-N-prop-2-ynyl-benzamide (intermediate 12) (48 mg, 0.097 mmol) is suspended in dichloromethane (2 mL) and degassed with a stream of argon. gold(III)-chloride (1.2 mg, 0.004 mmol) is added and the reaction is shaken at room temperature for 2 h. The solvent is evaporated and the residue is purified by reversed phase HPLC. Yield: 17 mg; ESI mass spectrum [M+H]+=495; Retention time HPLC: 1.09 min (HPLC method Z011_S03).

Workup

  1. customdegassed with a stream of argon
  2. customThe solvent is evaporated
  3. customthe residue is purified by reversed phase HPLC
  4. custom1.09 min (HPLC method Z011_S03)

Sources & evidence

ORD record
ord-4e01b123e1774a8fbcfd07a3d989326e
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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