1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11533845, compound

HRID 1668547Notes

Reaction equation

HRID 1668547 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([C:18]#[N:19])=[C:16]([NH2:20])[N:15]=[C:14]([S:21][CH2:22][C:23]3[N:28]=[C:27]([CH2:29][CH2:30][C:31](O)=[O:32])[CH:26]=[CH:25][CH:24]=3)[N:13]=2)=[CH:8][CH:7]=1)(=[O:4])[CH3:3].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.CCN=C=NCCCN(C)C.C(N(C(C)C)CC)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[NH2:20][C:16]1[N:15]=[C:14]([S:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([CH2:29][CH2:30][C:31]([N:38]3[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]3)=[O:32])[N:28]=2)[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:2](=[O:4])[CH3:3])=[CH:7][CH:8]=2)[C:17]=1[C:18]#[N:19]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 66852748HCID 66852748, compound

Product 1

HCID 11533845HCID 11533845, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound of Example 45 (100 mg) was suspended in 2 mL of methylene chloride. To the suspension were added 34 μL of N-methylpiperazine, 79 mg of WSC and 72 μL of diisopropyl-ethylamine, and the mixture was stirred at room temperature overnight. To the reaction mixture was added brine, the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (chloroform-methanol-28% aqueous ammonia=100:10:1) to give 95 mg of N-[4-(6-amino-5-cyano-2-{6-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]pyridin-2-ylmethylsulfanyl}pyrimidin-4-yl)phenyl]-acetamide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (chloroform-methanol-28% aqueous ammonia=100:10:1)

Sources & evidence

ORD record
ord-03711008d721416ba9b10fd0f3db7d8b
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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