Diisopropylethylamine → HCID 57917641, compound

HRID 1878403Notes

Reaction equation

HRID 1878403 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.Cl[CH2:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[C:39]([O:41][CH3:42])=[O:40]>C(#N)C>[CH3:47][O:46][C:45]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=1[CH2:35][N:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])=[CH:12][CH:13]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12853097Methyl 3-(chloromethyl)-4-methoxybenzoateHCID 57917584HCID 57917584, compound

Product 1

HCID 57917641HCID 57917641, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
45 °C

Procedure

1-Phenyl-3-(4-(piperazin-1-carbonyl)phenyl)urea (439 mg, 1.0 mmol) was stirred in acetonitrile (8 mL) at room temperature for 1 hour, N-Ethyl-N-isopropylpropan-2-amine (697 μl, 4 mmol) was added, followed by a solution of methyl 3-(chloromethyl)4-methoxy-benzoate (215 mg, 1.0 mmol) in acetonitrile (5 mL). The mixture was heated to 45° C. and stirred overnight. The mixture was concentrated under vacuum, diluted with dichloromethane (40 mL) and washed with saturated aqueous ammonium chloride (25 mL) and saturated aqueous sodium chloride (25 mL). The organic phase was dried on magnesium sulfate, filtered and concentrated under vacuum. The residue was submitted to silica chromatography (0-10% methanol in dichloromethane as eluant) to give the title compound (216 mg). MS (ESI) m/z 503.1 [M+H]+

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additiondiluted with dichloromethane (40 mL)
  3. washwashed with saturated aqueous ammonium chloride (25 mL) and saturated aqueous sodium chloride (25 mL)
  4. customThe organic phase was dried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c6675fb6d5e24748a5f5799a4898322a
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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