Diisopropylamine → Ethyl 4-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate

HRID 1746676Notes

Reaction equation

HRID 1746676 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.[NH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].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]([NH:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:21])=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 23365gamma-Aminobutyric acid ethyl esterHCID 594468454-(6-Chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride2×

Product 1

HCID 59446961Ethyl 4-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(6-chloropyrimidine-4-carboxamido)-3-methylbenzene-1-sulfonyl chloride (Intermediate 30, 1.2g; 3.47 mmol) in THF (100 ml) was treated with ethyl 4-aminobutanoate (720 mg; 4.34 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-3853dbba69364c5f9cbbc9ece4a1f7a7
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

Loading…