Reaction #1095851

ord-e8e5248374a34d1a80e74a20b7d41802

Reaction equation

CCN(CC)CCCC(C)Nc1cc(/C=C/c2ccccc2Cl)nc2cc(Cl)ccc12
2Q
CCN(CC)CCCC(C)Nc1cc(/C=C/c2ccccc2Cl)nc2cc(Cl)ccc12
aminoquinoline
O=C(O)CCc1c[nH]cn1
3-(1H-Imidazol-4-yl)propionic acid
O=C(n1ccnc1)n1ccnc1
CDI
CN(CCNC(=O)CCc1c[nH]cn1)CCNc1ccnc2cc(Cl)ccc12
N-(2-{[2-(7-Chloro-quinolin-4-ylamino)ethyl]methylamino}ethyl)-3-(1H-imidazol-4-yl)propionamide
Yield 23.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.STIRRINGto be stirred
  3. 3
    OtherAfter reaction overnight
  4. 4
    Filtrationthe reaction solution was filtered through a Kiriyama funnel
  5. 5
    ConcentrationThe filtrate was concentrated under a reduced pressure
  6. 6
    Otherto give a yellow oil
  7. 7
    Otherthis oil was purified by HPLC

Procedure

3-(1H-Imidazol-4-yl)propionic acid (140 mg, 1 mmol) was dissolved in dist THF, and a condensing agent CDI (200 mg, 1.3 mmol) was added to this solution. The solution was stirred. After two hours, 2Q (278 mg, 1 mmol) dissolved in dist THF was added and continued to be stirred. After reaction overnight, the reaction solution was filtered through a Kiriyama funnel. The filtrate was concentrated under a reduced pressure to give a yellow oil and this oil was purified by HPLC. Yield: 23%

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07973027B2uspto-grants-2011_07