Potassium tert-butoxide → tert-butyl 3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364062Notes

Reaction equation

HRID 1364062 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:20]([CH2:32]Cl)=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:21]4[CH2:22][CH2:23][N:24]([C:25]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:31])[CH2:32][C:20]4=[N:19][C:14]=3[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66958446HCID 66958446, compound

Product 1

HCID 66958454tert-butyl 3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method described in Part D of Example 365 was used to treat tert-butyl 2-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (23.55 g, 50.43 mmol) with potassium tert-butoxide (55.47 mL of a 1 M solution in THF) with the modification that crude product mixture was purified by normal phase prep HPLC on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 66-minute gradient from 0:100 to 7:93) to provide 20.87 g of tert-butyl 3-benzyloxy-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate. Material from a different run was used in Part I.

Workup

  1. customwas purified by normal phase prep HPLC on silica gel (
  2. washeluting with 2 N ammonia in methanol/chloroform in a 66-minute gradient from 0:100 to 7:93)

Sources & evidence

ORD record
ord-cb3bb6491f244def880a9cc9549f8541
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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