Trifluoroacetic acid → (R)-6-(3-aminopiperidin-1-yl)-2-(4-(diethylamino)phenylamino)nicotinamide

HRID 2044053Notes

Reaction equation

HRID 2044053 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28]C(=O)OC(C)(C)C)[CH2:23]2)=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C@@H:24]1[CH2:25][CH2:26][CH2:27][N:22]([C:7]2[CH:6]=[CH:5][C:4]([C:1]([NH2:2])=[O:3])=[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=3)[N:8]=2)[CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66832620(R)-tert-butyl 1-(5-carbamoyl-6-(4-(diethylamino)phenylamino)pyridin-2-yl)piperidin-3-ylcarbamate

Product 1

HCID 66832948(R)-6-(3-aminopiperidin-1-yl)-2-(4-(diethylamino)phenylamino)nicotinamideYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-tert-butyl 1-(5-carbamoyl-6-(4-(diethylamino)phenylamino) pyridin-2-yl)piperidin-3-ylcarbamate (1.41 g, 2.92 mmol) in CH2Cl2 (2 mL) was treated with TFA (4 ml) and stirred at rt for 4 h. The reaction mixture was concentrated and the residue dissolved in CH2Cl2 and washed with 1N NaOH and concentrated to give 1.07 g of (R)-6-(3-aminopiperidin-1-yl)-2-(4-(diethylamino)phenylamino)nicotinamide as a yellow solid. LCMS: (M+H)+=383.25.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with 1N NaOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbc2987108c246e387007949816d5d21
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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