Trifluoroacetic acid → HCID 86727409, compound

HRID 519043Notes

Reaction equation

HRID 519043 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:28][CH2:27][C:20]4=[N:21][NH:22][C:23](=[O:26])[CH:24]([CH3:25])[N:19]4[C:18]=3[CH:29]=2)[CH2:11][CH2:10][N:9]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[CH2:1]([CH:8]1[CH2:13][CH:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:28][CH2:27][C:20]4=[N:21][NH:22][C:23](=[O:26])[CH:24]([CH3:25])[N:19]4[C:18]=3[CH:29]=2)[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727408HCID 86727408, compound

Product 1

HCID 86727409HCID 86727409, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-benzyl-4-(1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)piperidine-1-carboxylate (0.147 g, 0.3 mmol) in DCM (2.5 mL) was added TFA (0.5 mL) and the mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo and EtOAc (2 mL) was added to the residue. The precipitate was collected by filtration and washed with EtOAc (1 mL) and petroleum ether (2 mL) to give 9-(2-benzylpiperidin-4-yl)-1-methyl-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one trifluoroacetic acid (0.030 g, 20% yield for three steps) as a solid. LC/MS (Table 1, Method 4) Rt=1.651 min; MS m/z: 391 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo and EtOAc (2 mL)
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with EtOAc (1 mL) and petroleum ether (2 mL)

Sources & evidence

ORD record
ord-9fef738e37c14d2a9eab2cce3ed5d9fb
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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