Benzyl [(3S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-bromoquinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate → 3-Amino-N-{4-[(3S)-3-aminopiperidin-1-yl]pyridin-3-yl}quinoline-2-carboxamide

HRID 924368Notes

Reaction equation

HRID 924368 reaction equation
C(OC([NH:11][C:12]1[C:13]([C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[N:32]2[CH2:37][CH2:36][CH2:35][C@H:34]([NH:38]C(=O)OCC3C=CC=CC=3)[CH2:33]2)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C:12]1[C:13]([C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][C:31]=2[N:32]2[CH2:37][CH2:36][CH2:35][C@H:34]([NH2:38])[CH2:33]2)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

4

Reactant 1

HCID 86726859Benzyl [(3S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-bromoquinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

Product 1

HCID 778442103-Amino-N-{4-[(3S)-3-aminopiperidin-1-yl]pyridin-3-yl}quinoline-2-carboxamideYield 16.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl [(3S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-bromoquinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (from step 5 in Example 1, 51.3 mg, 0.0723 mmol) in MeOH (2.0 mL), 10 wt % Pd on carbon (8.3 mg, 0.0078 mmol) was added. The mixture was stirred at room temperature under hydrogen (1 atm.) for 15 h. The reaction mixture was then filtered through a pad of diatomaceous earth, eluted with MeOH and then concentrated under reduced pressure. The resulting residue was purified using RP-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 as a yellow solid (4.3 mg, 16%). LCMS calc. for C20H23N6O (M+H)+: m/z=363.2. found 363.2.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  2. washeluted with MeOH
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified
  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-73f927e772bb4391a4f0f4d23d6b5c47
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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