Diisopropylethylamine → HCID 86732333, compound

HRID 517214Notes

Reaction equation

HRID 517214 reaction equation
C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.[CH3:15][O+:16]([CH3:18])C.[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:43]2C(=O)[CH2:47][CH2:46][CH2:45][C:44]=2[OH:50])[NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=2)=[O:30])=[CH:23][CH:22]=1)#[N:20]>ClCCl>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([C:43]2[C:44](=[O:50])[CH2:45][CH2:46][CH2:47][C:15]=2[O:16][CH3:18])[NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([C:39]([F:40])([F:42])[F:41])[CH:33]=2)=[O:30])=[CH:23][CH:22]=1)#[N:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 86732331HCID 86732331, compound2×

Product 1

HCID 86732333HCID 86732333, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-Diisopropylethylamine (450 μL, 2.59 mmol) and trimethyloxonium tetrafluoroborate (331 mg, 2.24 mmol) are added to a mixture of 1-((4-cyanophenyl)(2-hydroxy-6-oxocyclohex-1-enyl)methyl)-3-(4-fluoro-3-(trifluoromethyl)phenyl)urea (intermediate 44, 500 mg, 1.12 mmol) in dichloromethane (4.0 mL), and the mixture is stirred at room temperature for 20 min Dichloromethane (20 mL) is added, and the phases are separated. The organic layer is washed three times with water and concentrated under reduced pressure. Yield: 567 mg; ESI mass spectrum [M+H]+=462; Retention time HPLC: 1.09 min (Z018_S04).

Workup

  1. additionis added
  2. customthe phases are separated
  3. washThe organic layer is washed three times with water
  4. concentrationconcentrated under reduced pressure
  5. custom1.09 min (Z018_S04)

Sources & evidence

ORD record
ord-b6a0c70d90434653835c8f8f7c73639c
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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