Hydrochloric Acid → (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride

HRID 420674Notes

Reaction equation

HRID 420674 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6](=[O:12])[N:5]3[C@H:13]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18][CH2:17]4)[CH2:14][N:3]1[C:4]=23.[ClH:30].CO>C(Cl)(Cl)Cl>[ClH:30].[ClH:30].[NH2:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][C@H:13]2[N:5]3[C:4]4[N:3]([C:2](=[O:1])[CH:11]=[CH:10][C:9]=4[CH:8]=[CH:7][C:6]3=[O:12])[CH2:14]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 582009021,1-Dimethylethyl (1-{[(1R)-4,9-dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-piperidinyl)carbamate

Product 1

HCID 66658412(1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochlorideYield 114.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1,1-dimethylethyl (1-{[(1R)-4,9-dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-piperidinyl)carbamate (see Example 1 (i) above) (4.282 g, 10.69 mmol) in CHCl3 (20 ml) under Ar at room temperature was treated with HCl (4M solution in 1,4-dioxane, 20 ml, 80 mmol) and stirred at rt for 15 min, MeOH (20 ml) was then added. After stirred for 15 min, the reaction was evaporated and triturated with Et2O (20 ml). The obtained solid was dried in vacuo to give (1R)-1-[(4-amino-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione dihydrochloride (4.55 g, 12.21 mmol, 100%) as a yellow powder.

Workup

  1. customat room temperature
  2. stirringAfter stirred for 15 min
  3. customthe reaction was evaporated
  4. customtriturated with Et2O (20 ml)
  5. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-78fac084d60d448dac010b059df9c988
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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