Trifluoroacetic acid → HCID 53258444, compound

HRID 524127

Reaction equation

HRID 524127 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-9d8d5f5af16b407285fe83a5006babd4
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Linked notes

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