2-Isopropylaniline → N-(2-isopropylphenyl)-3-[6-(4-t-butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionamide

HRID 1418333Notes

Reaction equation

HRID 1418333 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:18]=[C:17]([O:27][CH2:28][CH2:29][C:30](O)=[O:31])[C:16]=2[O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[O:40][CH3:41])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.O.[CH:53]([C:56]1[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=1[NH2:58])([CH3:55])[CH3:54].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(Cl)Cl>[CH:53]([C:56]1[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=1[NH:58][C:30](=[O:31])[CH2:29][CH2:28][O:27][C:17]1[C:16]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[O:40][CH3:41])=[C:15]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:6][CH:7]=2)(=[O:12])=[O:13])[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:18]=1)([CH3:55])[CH3:54]

Participants

6

Reactant 4

HCID 125612-IsopropylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 153811033-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid

Product 1

HCID 9896468N-(2-isopropylphenyl)-3-[6-(4-t-butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionamideYield 101.3%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

3-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid (80 mg) was dissolved in dimethylformamide-methylene chloride (1:1, 6 ml). N-Hydroxybenzotriazole·H2O (42.2 mg), 2-isopropylaniline (133.2 mg), and 1-(3-dimethylaminopropyl) -3-ethylcarbodiimide-HCl (32.6 mg) were added to the mixture. The reaction mixture was stirred overnight at room temperature. After the solvent was evaporated, ethyl acetate was added. The organic layer was successively washed with sat. aq. NaHCO3, 0.5N-HCl, and brine, was dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1), to thereby obtain 97.2 mg (yield: 100%) of the title compound as a colorless oil.

Workup

  1. customAfter the solvent was evaporated
  2. additionethyl acetate was added
  3. washThe organic layer was successively washed with sat. aq. NaHCO3, 0.5N-HCl, and brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-e458a8d5809040ab817a2e9d0c7f04b5
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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