Triethylamine → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-[4-(1H-1,2,4-triazol-1-ylmethyl)phenyl]pyrimidine-4-carboxamide

HRID 1746800Notes

Reaction equation

HRID 1746800 reaction equation
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:28]1([CH2:33][C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)[CH:32]=[N:31][CH:30]=[N:29]1>C(Cl)Cl>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:38][C:37]3[CH:39]=[CH:40][C:34]([CH2:33][N:28]4[CH:32]=[N:31][CH:30]=[N:29]4)=[CH:35][CH:36]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8212191-(4-Aminobenzyl)-1,2,4-triazoleHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2×

Product 1

HCID 594469666-[cyclohexyl(cyclopropylmethyl)amino]-N-[4-(1H-1,2,4-triazol-1-ylmethyl)phenyl]pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(cyclohexyl(cyclopropylmethyl)amino)pyrimidine-4-carboxylic acid (Intermediate 13, 100 mg; 0.36 mmol) in DCM (4 ml) was treated with polymer-supported Mukaiyama reagent (400 mg) followed by triethylamine (100 mL; 0.73 mmol) and 4-((1H-1,2,4-triazol-1-yl)methyl)aniline (Maybridge, 63.2 mg; 0.36 mmol). After stirring at RT for 24 hours the mixture was filtered and washed with saturated sodium bicarbonate solution. The organic phase was 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 to give the title compound as a white solid.

Workup

  1. filtrationwas filtered
  2. washwashed with saturated sodium bicarbonate solution
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography (silica)
  5. washeluting with petroleum ether containing
  6. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-7addb6d3b1394479bb7ffd5d9405c49a
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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