Hydrochloric Acid → 3-Benzyloxy-8,9,10,11-tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

HRID 1364071Notes

Reaction equation

HRID 1364071 reaction equation
[ClH:1].CO.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]3[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18][N:17]3[C:13]=2[C:12]2[C:7](=[CH:8][C:9]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:10][CH:11]=2)[N:6]=1>O1CCOCC1>[ClH:1].[CH2:30]([O:29][C:9]1[CH:8]=[C:7]2[C:12]([C:13]3[N:17]4[CH2:18][CH2:19][NH:20][CH2:21][C:16]4=[N:15][C:14]=3[C:5]([NH2:4])=[N:6]2)=[CH:11][CH:10]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66958130tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Product 1

HCID 669583983-Benzyloxy-8,9,10,11-tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (20 mL of a 4 N solution in 1,4-dioxane) and methanol (20 mL) were added to tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (4.45 g, 9.98 mmol, prepared by the methods described in Example 368 Parts A through I), and the reaction was stirred at ambient temperature overnight. A precipitate was present and was isolated by filtration and washed with cold methanol. The solid was then recrystallized from methanol, isolated by filtration, washed with diethyl ether, and dried overnight under vacuum at 65° C. to provide 3.89 g of 3-benzyloxy-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride as a white solid.

Workup

  1. customprepared by the methods
  2. customwas isolated by filtration
  3. washwashed with cold methanol
  4. customThe solid was then recrystallized from methanol
  5. customisolated by filtration
  6. washwashed with diethyl ether
  7. customdried overnight under vacuum at 65° C.

Sources & evidence

ORD record
ord-46832aead838433ebc504dde06d4cfc6
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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