Trifluoroacetic acid → HCID 66832821, compound

HRID 2044082Notes

Reaction equation

HRID 2044082 reaction equation
[C:1]([C:4]1[C:5]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[O:32])=[CH:27][CH:26]=2)=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([NH:16]C(=O)OC(C)(C)C)[CH2:11]2)=[N:8][CH:9]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C@@H:12]1[CH2:13][CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[C:5]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[O:32])=[CH:27][CH:26]=3)[C:4]([C:1]([NH2:2])=[O:3])=[CH:9][N:8]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66833305HCID 66833305, compound

Product 1

HCID 66832821HCID 66832821, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 1-(5-carbamoyl-4-(4-(morpholine-4-carbonyl)phenylamino)pyridin-2-yl)piperidin-3-ylcarbamate (110 mg, 0.210 mmol) in CH2Cl2 (2 mL) was treated with TFA (4 mL, 51.9 mmol) and stirred at rt for 4 hrs. The mixture is evaporated to dryness and the residue was dissolved in CH2Cl2 and washed with bicarbonate, water, and brine. Concentrated to give 72 mg of (R)-6-(3-aminopiperidin-1-yl)-4-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide.

Workup

  1. customThe mixture is evaporated to dryness
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with bicarbonate, water, and brine
  4. concentrationConcentrated

Sources & evidence

ORD record
ord-cd1bff528db94888b392546cb79a88c5
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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