1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59447751, compound

HRID 1678429Notes

Reaction equation

HRID 1678429 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:6]=[C:5]([N:16]2[CH2:21][CH2:20][CH2:19][CH:18]([C:22](O)=[O:23])[CH2:17]2)[N:4]=1.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH2:34].CN(C1C=CC=CN=1)C.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C.CO>[F:25][C:26]([F:35])([F:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH:34][C:22]([CH:18]1[CH2:19][CH2:20][CH2:21][N:16]([C:5]2[N:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([N:9]3[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]3)[N:6]=2)[CH2:17]1)=[O:23]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 764472-(Trifluoromethyl)benzylamineHCID 67338599HCID 67338599, compound

Product 1

HCID 59447751HCID 59447751, compoundYield 26.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-[4-(methylamino)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-3-piperidinecarboxylic acid (0.18 g, 0.55 mmol, 1.0 equiv), [(2-trifluoromethyl-phenyl)methyl]amine (0.12 g, 0.68 mmol, 1.25 equiv), and dimethylaminopyridine (DMAP, 14 mg, 0.11 mmol, 0.2 equiv) in CH2Cl2 and DMF was cooled to ˜0° C. using an ice bath. Next EDCI (0.16 g, 0.82 mmol, 1.5 equiv) was added. The reaction mixture was stirred at 0° C. for 30 min and at room temperature for an additional 2 hours. The reaction was monitored by HPLC. The solution was then diluted with CH2Cl2 and washed with saturated aqueous NaCl. The organic layer was dried over Na2SO4, and concentrated to provide the crude product. The crude product was dissolved in methanol and purified by HPLC to afford 73 mg of the title compound. MS (ES+): m/e 493.3 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customto provide the crude product
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-c19d30ef7319403a97377f76a536fe51
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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