Trifluoroacetic acid → (R)-1-methyl-9-((3-methylazetidin-3-yl)amino)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid

HRID 519058Notes

Reaction equation

HRID 519058 reaction equation
[CH3:1][C:2]1([NH:13][C:14]2[C:15]([C:30]([F:33])([F:32])[F:31])=[CH:16][C:17]3[O:28][CH2:27][C:20]4=[N:21][NH:22][C:23](=[O:26])[C@@H:24]([CH3:25])[N:19]4[C:18]=3[CH:29]=2)[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[CH3:25][C@@H:24]1[C:23](=[O:26])[NH:22][N:21]=[C:20]2[CH2:27][O:28][C:17]3[CH:16]=[C:15]([C:30]([F:32])([F:31])[F:33])[C:14]([NH:13][C:2]4([CH3:1])[CH2:3][NH:4][CH2:5]4)=[CH:29][C:18]=3[N:19]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727421(R)-tert-butyl 3-methyl-3-((1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate

Product 1

HCID 86727422(R)-1-methyl-9-((3-methylazetidin-3-yl)amino)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-methyl-3-((1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate (Enantiomer 1, SFC (Table 1, Method 16) Rt: 6.686 min, 0.270 g, 0.55 mmol) in DCM (10 mL) was added TFA (2 mL) and the mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo to give (R)-1-methyl-9-((3-methylazetidin-3-yl)amino)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid (Example #100-1, Enantiomer 1, SFC (Table 1, Method 18) Rt: 9.62 min, 0.275 g, 99%) as a pale solid. LC/MS (Table 1, Method 5) Rt=2.005 min; MS m/z: 370 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7ac8bfd65c2d4dec8c47ac8e9a0d5117
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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