Trifluoroacetic acid → HCID 53258444, compound

HRID 240294

Reaction equation

HRID 240294 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[N:8][N:7]=[C:6]1[N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19]C(=O)OC(C)(C)C)[CH2:14]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][N:13]([C:6]2[N:5]([CH2:4][C:3]3[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:2]=3[Cl:1])[C:10](=[O:11])[C:9]([CH3:12])=[N:8][N:7]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58328537(R)-tert-butyl 1-(4-(2-chloro-5-fluorobenzyl)-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)piperidin-3-ylcarbamate

Product 1

HCID 53258444HCID 53258444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 1-(4-(2-chloro-5-fluorobenzyl)-6-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl)piperidin-3-ylcarbamate (31, 44 mg) in dichloromethane (1 mL) was added TFA (0.4 mL), and the mixture was stirred at RT for 1.5 h. The mixture was carefully neutralized with NaHCO3 (aq, saturated), and extracted with CH2Cl2 (10 mL×3). The combined extracts were dried over Na2SO4 and concentrated to give (R)-3-(3-aminopiperidin-1-yl)-4-(2-chloro-5-fluorobenzyl)-6-methyl-1,2,4-triazin-5(4H)-one (32). MS: m/z, 352 (100%, M+1), 354 (33%).

Workup

  1. extractionextracted with CH2Cl2 (10 mL×3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9a8ce73944e54f74a362d5c09102a6ff
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Linked notes

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