Hydrochloric Acid → 9-(azetidin-3-ylamino)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one hydrochloric acid

HRID 519082Notes

Reaction equation

HRID 519082 reaction equation
[ClH:1].CCOC(C)=O.C(OC([N:15]1[CH2:18][CH:17]([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26]4[N:27]3[CH:30]([CH3:35])[C:31](=[O:34])[NH:32][N:33]=4)=[CH:22][CH:21]=2)[CH2:16]1)=O)(C)(C)C>>[ClH:1].[NH:15]1[CH2:16][CH:17]([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26]4[N:27]3[CH:30]([CH3:35])[C:31](=[O:34])[NH:32][N:33]=4)=[CH:22][CH:21]=2)[CH2:18]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86727448tert-butyl 3-(1-methyl-2-oxo-2,3,5,6-tetrahydro-1H-[1,2,4]triazino[4,3-a]quinolin-9-ylamino)azetidine-1-carboxylate

Product 1

HCID 867274499-(azetidin-3-ylamino)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one hydrochloric acidYield 95%

Procedure

To a solution of HCl in EtOAc (4M, 5 mL, 20 mmol) was added slowly tert-butyl-3-(1-methyl-2-oxo-2,3,5,6-tetrahydro-1H-[1,2,4]triazino[4,3-a]quinolin-9-ylamino)azetidine-1-carboxylate (0.022 g, 0.057 mmol) and the reaction mixture was stirred at ambient temperature for 2 h. The solution was concentrated in vacuo to give 9-(azetidin-3-ylamino)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one hydrochloric acid (0.015 g, 95%). LC/MS (Table 1, Method 5) Rt=2.252 min; MS m/z: 286 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d35e88e40a764623a2ff21fcc51ccb10
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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