Diisopropylethylamine → 1-((4-Cyanophenyl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea

HRID 517194Notes

Reaction equation

HRID 517194 reaction equation
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.C(N(CC)C(C)C)(C)C.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:42]2C(=O)[CH2:46][CH2:45][CH2:44][C:43]=2[OH:49])[NH:28][C:29]([NH:31][C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][N:33]=2)=[O:30])=[CH:23][CH:22]=1)#[N:20]>>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:42]2[C:43](=[O:49])[CH2:44][CH2:45][CH2:46][C:6]=2[O:7][CH3:9])[NH:28][C:29]([NH:31][C:32]2[CH:37]=[C:36]([C:38]([F:39])([F:41])[F:40])[CH:35]=[CH:34][N:33]=2)=[O:30])=[CH:23][CH:22]=1)#[N:20]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 867323121-((4-Cyanophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea2×

Product 1

HCID 867323131-((4-Cyanophenyl)(2-methoxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea

Procedure

Trimethyloxonium tetrafluoroborate (185 mg, 1.25 mmol) is added to a solution of N,N-diisopropylethylamine (210 μL, 1.21 mmol) and 1-((4-cyanophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(4-(trifluoromethyl)pyridin-2-yl)urea (intermediate 24, 264 mg, 0.613 mmol). The mixture is stirred at room temperature for 1 h and extracted with water. The organic phase is dried over Na2SO4 and concentrated under reduced pressure. Yield: 200 mg; ESI mass spectrum [M+H]+=445, Retention time HPLC: 1.08 min (V011_S01).

Workup

  1. extractionextracted with water
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custom1.08 min (V011_S01)

Sources & evidence

ORD record
ord-54a8b7e2912d4e9384a0a7f45815a61d
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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