1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67435329, compound

HRID 1803388Notes

Reaction equation

HRID 1803388 reaction equation
Cl[CH2:2][C:3]1[N:4]([C@H:16]([CH2:28][NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1.N12CCCN=C1CCCCC2>C(Cl)Cl>[CH3:33][S:30]([N:29]1[CH2:28][C@H:16]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[N:4]2[C:5]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]=[CH:7][C:6]=3[N:15]=[C:3]2[CH2:2]1)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86619540HCID 86619540, compound

Product 1

HCID 67435329HCID 67435329, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (4S)-4-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-5-[(methylsulfonyl)amino]pentylcarbamate (8.08 g, 16.3 mmol) was dissolved in 200 mL of CH2Cl2 and treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.91 mL, 19.5 mmol) After 1 hour, the reaction mixture was washed successively with H2O and brine and the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 3% methanol/CHCl3) gave tert-butyl 3-[(11S)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (6.16 g) as a light yellow foam.

Workup

  1. washthe reaction mixture was washed successively with H2O and brine
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6abc6903c30542e9b2b4dd0a0d1ff536
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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