Water → 1-((4-Cyano-2-fluorophenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517209Notes

Reaction equation

HRID 517209 reaction equation
F[B-](F)(F)F.C([O+:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:36]2C(=O)C[CH2:39][CH2:38][C:37]=2[OH:43])[NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[O:24])=[C:17]([F:44])[CH:16]=1)#[N:14].C(N(CC)C(C)C)(C)C.O>ClCCl>[C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:36]2[C:37](=[O:43])[CH2:38][CH2:39][CH2:12][C:11]=2[O:8][CH2:9][CH3:10])[NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)=[O:24])=[C:17]([F:44])[CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2723982Triethyloxonium tetrafluoroborateHCID 867323291-((4-Cyano-2-fluorophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 867323301-((4-Cyano-2-fluorophenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyloxonium tetrafluoroborate (1.60 g, 8.42 mmol) is added to a solution of 1-((4-cyano-2-fluorophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 40 1.80 g, 4.02 mmol) and N,N-diisopropylethylamine (1.60 mL, 9.2 mmol) in dichloromethane (15 mL), and the mixture is stirred at room temperature for 20 min Water is added, and the phases are separated. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. Yield: 1.82 g; ESI mass spectrum [M+H]+=476, Retention time HPLC: 1.11 min (Z018_S04).

Workup

  1. additionis added
  2. customthe phases are separated
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custom1.11 min (Z018_S04)

Sources & evidence

ORD record
ord-aefe943f0c6f43ca8b1189f41dff24a5
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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