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1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(7-tert-butyl-3,4-dihydro-2H-chromen-4-yl)-N'-quinolin-8-ylurea

HRID 2092150
Notes
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Reaction equation

HRID 2092150 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)=[O:4].[C:18]([C:22]1[CH:31]=[C:30]2[C:25]([CH:26]([NH2:32])[CH2:27][CH2:28][O:29]2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].N12CCCN=C1CCCCC2>C(#N)C>[C:18]([C:22]1[CH:31]=[C:30]2[C:25]([CH:26]([NH:32][C:3]([NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:15]=3[N:14]=[CH:13][CH:12]=[CH:11]4)=[O:4])[CH2:27][CH2:28][O:29]2)=[CH:24][CH:23]=1)([CH3:21])([CH3:19])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27974822,2,2-Trichloro-N-(quinolin-8-YL)acetamideHCID 672368437-tert-Butyl-chroman-4-ylamine

Product 1

HCID 53251493N-(7-tert-butyl-3,4-dihydro-2H-chromen-4-yl)-N'-quinolin-8-ylureaYield 14.4%

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

A mixture of the product of Example 3A (145 mg, 0.5 mmol), the product of Example 1C (103 mg, 0.5 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 190 mg, 1.25 mmol) in acetonitrile (15 mL) was heated at reflux for 3.5 hours, cooled, and the acetonitrile removed under reduced pressure. The residue was taken up in ethyl acetate and washed with water. The isolated organic layer was dried with magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting residue was purified by reverse-phase HPLC (acetonitrile/water) to give 27 mg of the title compound (14% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.37 (s, 1H), 8.83 (dd, J=4.1 and 1.7 Hz, 1H), 8.54 (dd, J=7.3 and 1.9 Hz, 1H), 8.34 (dd, J=8.5 and 1.7 Hz, 1H), 7.91 (d, J=7.8 Hz, 1H), 7.55-7.60 (m, 1H), 7.46-7.53 (m, 2H), 7.22 (d, J=8.1 Hz, 1H), 6.94 (dd, J=8.1 and 2.0 Hz, 1H), 6.77 (d, J=2.0 Hz, 1H), 4.87-4.93 (m, 1H), 4.22-4.29 (m, 1H), 4.12-4.20 (m, 1H), 2.07-2.16 (m, 1H), 1.91-2.00 (m, 1H), 1.24 (s, 9H). MS (ESI) m/e 376 (M+H)+. Calcd. For C23H25N3O2.0.35; CF3CO2H, C, 68.53; H, 6.15; N, 10.12. Found C, 68.33; H, 6.00; N, 10.00.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperaturecooled
  3. customthe acetonitrile removed under reduced pressure
  4. washwashed with water
  5. dry with materialThe isolated organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe resulting residue was purified by reverse-phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-b4327674b5144670978ad4e9ad5db34c
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440691B2

Reaction notes

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