Diisopropylamine → methyl 2-(4-(6-chloropyrimidine-4-carboxamido)-N,3-dimethylphenylsulfonamido)acetate

HRID 1946695Notes

Reaction equation

HRID 1946695 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1.[CH3:22][NH:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].C(NC(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH3:22])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 83545Sarcosine methyl esterHCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride2×

Product 1

HCID 59446951methyl 2-(4-(6-chloropyrimidine-4-carboxamido)-N,3-dimethylphenylsulfonamido)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 1.2 g; 3.47 mmol) in THF (100 ml) was treated with methyl 2-(methylamino)acetate (666 mg; 4.77 mmol) and diisopropylamine (2 ml; 14.3 mmol). After stirring at RT for 18 hours the solvent was removed in vacuo and the residue redissolved in DCM and washed with water. The organic extracts were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc. The title product was obtained as a white solid.

Workup

  1. customwas removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (silica)
  6. washeluting with petroleum ether containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-b31837db262e4ed2a7d08fd4ec16df91
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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