Tert-butyl 4-(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)piperidine-1-carboxylate → 1-methyl-9-(piperidin-4-yl)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one

HRID 519101Notes

Reaction equation

HRID 519101 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:9][O:10][C:11]3[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:14]([CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[CH:13][C:12]=3[N:3]12>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:9][O:10][C:11]3[CH:16]=[C:15]([C:17]([F:18])([F:20])[F:19])[C:14]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:13][C:12]=3[N:3]12

Participants

4

Reactant 1

HCID 86727472Tert-butyl 4-(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)piperidine-1-carboxylate

Product 1

HCID 867274731-methyl-9-(piperidin-4-yl)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-(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)piperidine-1-carboxylate (0.01 g, 0.021 mmol) in DCM (5 mL) and TFA (1 mL) was stirred for 1 h at ambient temperature. The solvent was removed in vacuo to give 1-methyl-9-(piperidin-4-yl)-8-(trifluoromethyl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoacetic acid salt as a pale yellow solid (0.01 g, 97%). LC/MS (Table 1, Method 5) Rt=3.057 min.; MS m/z: 369 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ea60a46e6c194f6dad52ce92dc0ab111
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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