Dimethylformamide → HCID 44213936, compound

HRID 1418334Notes

Reaction equation

HRID 1418334 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].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1>C(Cl)Cl>[N:55]1[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=1[NH:53][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]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:13])=[O:12])[N:20]=[C:19]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 104392-AminopyridineHCID 65578Oxalyl chlorideHCID 153811033-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid

Product 1

HCID 44213936HCID 44213936, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[6-(4-t-Butylphenylsulfonylamino)-5-(2-methoxyphenoxy)-2-morpholino-4-pyrimidinyloxy]propionic acid (121 mg) was dissolved in methylene chloride (0.9 ml). Oxalyl chloride (27 mg) and dimethylformamide (1 droplet) were added, and the mixture was stirred for 30 minutes at room temperature. 2-Aminopyridine (38 mg) was added, and the mixture was stirred overnight at room temperature. After the solvent was evaporated, ethyl acetate was added. The organic layer was successively washed with 0.5N-HCl, sat. aq. NaHCO3, and brine, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1), to thereby obtain 51 mg (yield: 37%) of the title compound as a white powder.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customAfter the solvent was evaporated
  3. additionethyl acetate was added
  4. washThe organic layer was successively washed with 0.5N-HCl, sat. aq. NaHCO3, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-1ad49222903e445c89dd92e534d14971
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Reaction notes

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