Benzyl {2-[({4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-morpholin-4-ylquinolin-3-yl}carbamate → 3-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-morpholin-4-ylquinoline-2-carboxamide

HRID 924459Notes

Reaction equation

HRID 924459 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([C:8]([F:11])([F:10])[F:9])[CH2:5][N:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[C:30]([NH:31]C(=O)OCC3C=CC=CC=3)=[CH:29][C:28]3[C:23](=[CH:24][C:25]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:26][CH:27]=3)[N:22]=2)=[O:20])[CH2:3]1>Br.CC(O)=O>[NH2:31][C:30]1[C:21]([C:19]([NH:18][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:12]=2[N:4]2[CH2:5][C@H:6]([C:8]([F:10])([F:11])[F:9])[CH2:7][C@H:2]([NH2:1])[CH2:3]2)=[O:20])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[C:25]([N:42]1[CH2:43][CH2:44][O:45][CH2:46][CH2:47]1)[CH:24]=2

Participants

4

Reactant 1

HCID 86726902Benzyl {2-[({4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-morpholin-4-ylquinolin-3-yl}carbamate

Product 1

HCID 867269033-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-morpholin-4-ylquinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A mixture of benzyl {2-[({4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-morpholin-4-ylquinolin-3-yl}carbamate (0.005 g, 0.008 mmol) in 2 mL of 4 M HBr in AcOH was stirred at room temperature for 2 h. The solution was then concentrated under reduced pressure and the residue was treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution. The resulting mixture was filtered and the filtrate was purified by preparative HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.) to afford the title compound. LCMS calc. for C25H29F3N7O2 [M+H]+: m/z=516.2. found: 516.3.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. additionthe residue was treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate was purified by preparative HPLC (XBridge™ C18 column
  5. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-564c50c1437a4d4a80c602c55a521f72
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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