Diisopropylethylamine → 2-[2-(4-Benzo[1,3]dioxol-5-yl-piperazin-1-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl) amide

HRID 1822792Notes

Reaction equation

HRID 1822792 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:26])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH3:24])[N:18]=[C:17](Cl)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2].Cl.Cl.[O:29]1[C:33]2[CH:34]=[CH:35][C:36]([N:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[CH:37][C:32]=2[O:31][CH2:30]1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:26])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][CH3:24])[N:18]=[C:17]([N:41]2[CH2:42][CH2:43][N:38]([C:36]3[CH:35]=[CH:34][C:33]4[O:29][CH2:30][O:31][C:32]=4[CH:37]=3)[CH2:39][CH2:40]2)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 221700331-Benzo[1,3]dioxol-5-yl-piperazine dihydrochlorideHCID 235686202-(6-Butyl-2-chloropyrimidin-4-ylamino)-4-methypentanoic acid (3-ethoxypropyl)amide

Product 1

HCID 235685942-[2-(4-Benzo[1,3]dioxol-5-yl-piperazin-1-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl) amideYield 15.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(6-Butyl-2-chloro-pyrimidin-4-ylamino)-4-methylpentanoic acid (3-ethoxypropyl)amide (10 mg), 1-benzo[1,3]dioxol-5-yl-piperazine dihydrochloride (25 mg), and N,N-diisopropylethylamine (50 μL) were stirred for 24 h in 1 mL methyl sulfoxide at 100° C. The solution was cooled to room temperature and diluted with ethyl acetate (30 mL), then washed 4 times with 30 mL aliquots of a saturated aqueous solution of sodium chloride. Semi-preparative HPLC followed by silica gel chromatography (gradient: 2–4% methyl alcohol in methylene chloride) provided 2.2 mg of 2-[2-(4-benzo[1,3]dioxol-5-yl-piperazin-1-yl)-6-butylpyrimidin-4-ylamino]-4-methylpentanoic acid (3-ethoxypropyl) amide. ESI-MS (m/z) 555 [M+H]+.

Workup

  1. washwashed 4 times with 30 mL aliquots of a saturated aqueous solution of sodium chloride

Sources & evidence

ORD record
ord-a07f95b053b64778912028ff2c251894
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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