Diisopropylamine → Tert-butyl 3-(4-(6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)propanoate

HRID 1746769Notes

Reaction equation

HRID 1746769 reaction equation
Cl[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:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:19])=[O:18])=[CH:13][C:12]=2[CH3:30])=[O:9])[CH:3]=1.C(NC(C)C)(C)C.[CH:38]1([CH2:41][NH:42][CH2:43][CH2:44][CH3:45])[CH2:40][CH2:39]1>C(O)C>[CH:38]1([CH2:41][N:42]([CH2:43][CH2:44][CH3:45])[C:2]2[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:19])=[O:18])=[CH:13][C:12]=3[CH3:30])=[O:9])[CH:3]=2)[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 117787Cyclopropanemethanamine, N-propyl-HCID 59447084Tert-butyl 3-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)propanoate2×

Product 1

HCID 68486490Tert-butyl 3-(4-(6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A solution of tert-butyl 3-(4-(6-chloropyrimidine-4-carboxamido)-3-methylphenylsulfonamido)propanoate (Intermediate 34, 140 mg; 0.31 mmol) and diisopropylamine (105.5 mL; 0.61 mmol) in ethanol (4 ml) was treated with N-(cyclopropylmethyl)propan-1-amine (45.3 mg; 0.4 mmol). The mixture was heated to 160° C. in a microwave for 1 hour and then filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give tert-butyl 3-(4-(6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxamido)-3-methylphenylsulfonamido)propanoate which was used directly without any further purification. The residue was redissolved in DCM (4.5 ml) and treated with TFA (0.5 ml). After stirring at RT for 2 hours the solvent was removed in vacuo to give the title compound as an off-white solid.

Workup

  1. filtrationfiltered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography (silica)
  4. washeluting with petroleum ether containing
  5. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-b88e7a00d16b4cddb5c9e6d14c0eb14b
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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