Diisopropylethylamine → HCID 23568630, compound

HRID 1822786Notes

Reaction equation

HRID 1822786 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:5]=[C:4]([S:16][CH3:17])[N:3]=1.[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:32])[CH:26]([NH2:31])[CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:19].C(N(C(C)C)CC)(C)C>CS(C)=O>[CH2:18]([O:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:32])[CH:26]([NH:31][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:5]=[C:4]([S:16][CH3:17])[N:3]=1)[CH2:27][CH:28]([CH3:29])[CH3:30])[CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22170008HCID 22170008, compoundHCID 22170051HCID 22170051, compound

Product 1

HCID 23568630HCID 23568630, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-6-cyclohexyloxymethyl-2-methylsulfanyl-pyrimidine, the hydrochloride salt of 2-amino-4-methylpentanoic acid (3-ethoxypropyl)amide (60 mg), and diisopropylethylamine (61 mg) in dimethylsulfoxide (0.5 mL) was heated at 95° C. for 16 h. The mixture was partitioned in water and ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (30% ethyl acetate in hexanes) to give 2-(6-cyclohexyloxymethyl-2-methylsulfanyl-pyrimidin-4-ylamino)-4-methyl-pentanoic acid (3-ethoxy-propyl)-amide (12 mg).

Workup

  1. customThe mixture was partitioned in water
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-527ff1b532cc4a03892150487701053c
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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