Phenyl carbamate → HCID 59420858, compound

HRID 499205Notes

Reaction equation

HRID 499205 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:18]=[C:17]([F:28])[CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C1([O:35][C:36](=O)[NH2:37])C=CC=CC=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CS(C)=O.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:13])[NH:14][C:15]2[CH:20]=[C:19]([CH:18]=[C:17]([F:28])[CH:16]=2)[O:21][CH:22]2[CH2:23][CH2:24][N:25]([C:36]([NH2:37])=[O:35])[CH2:26][CH2:27]2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 69322Phenyl carbamateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 68457459HCID 68457459, compound

Product 1

HCID 59420858HCID 59420858, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Nitrogen gas is bubbled trough a solution of 1-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-{3-fluoro-5-(piperidin-4-yloxy)-phenyl}-urea (390.6 mg, 1.0 mmol) and carbamic acid phenyl ester (140.6 mg, 1.0 mmol) in DMSO (2 mL) for 5 minutes. Next, N,N-diisopropylethylamine (350 μL, 2.0 mmol) is added. After stirred at 85° C. overnight, the reaction mixture is distributed between ethyl acetate (15 mL) and saturated sodium bicarbonate (50 mL). The aqueous phase is isolated and extracted with ethyl acetate (2×15 mL). The combined organic phases are dried over sodium sulfate and concentrated. The residue is purified on a silica gel chromatography with hexanes and ethyl acetate to give a white solid (250 mg, 58% yield, ES+(m/z) 433.3 [M+H]).

Workup

  1. customThe aqueous phase is isolated
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified on a silica gel chromatography with hexanes and ethyl acetate
  6. customto give a white solid (250 mg, 58% yield, ES+(m/z) 433.3 [M+H])

Sources & evidence

ORD record
ord-1ed9d6ca3ba546b3a76c0a286677ce92
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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