4-Nitrophenyl chloroformate → HCID 68676084, compound

HRID 643153Notes

Reaction equation

HRID 643153 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH2:14]([O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][C@@H:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=1[CH3:36])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:37]1[CH2:42][CH2:41][CH:40]([N:43]2[C:47]3[CH:48]=[N:49][C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=4[C:46]=3[NH:45][C:44]2=[O:56])[CH2:39][CH2:38]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:56]=[C:44]1[N:43]([CH:40]2[CH2:39][CH2:38][N:37]([C:2]([O:35][C@@H:30]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][C:25]3[CH:24]=[C:23]([CH3:36])[C:22]([O:21][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:27]([CH3:28])[CH:26]=3)=[O:3])[CH2:42][CH2:41]2)[C:47]2[CH:48]=[N:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=3[C:46]=2[NH:45]1

Participants

6

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 183215593-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-oneHCID 67273374HCID 67273374, compound

Product 1

HCID 68676084HCID 68676084, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

Under a nitrogen atmosphere 1.28 g (6.36 mmol) 4-nitrophenyl chloroformate were added at RT to a solution of 0.78 g (6.36 mmol) 4-dimethylaminopyridine in 100 mL pyridine and the mixture was stirred for 1 h at RT. Then a solution of 2.00 g (6.36 mmol) methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate in 20 mL pyridine was added dropwise at RT and the reaction mixture was stirred for 2 h after the end of the addition. Then 1.71 g (6.36 mmol) 3-piperidin-4-yl-1,3-dihydro-imidazo[4,5-c]quinoline-2-one was added to the reaction mixture, which was then heated to 100° C. for 4 h. The precipitate formed was filtered off, the filtrate was evaporated down i.vac., the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution, the product being obtained as a precipitate. This was suction filtered and dried.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. additionafter the end of the addition
  3. temperaturewas then heated to 100° C. for 4 h
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customthe filtrate was evaporated down i.vac
  7. addition, the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution
  8. customthe product being obtained as a precipitate
  9. filtrationThis was suction filtered
  10. customdried

Sources & evidence

ORD record
ord-8b38c85137d74a43a2fc2a9d1393bcd4
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

Loading…