Benzyl [2-[({4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(3-oxopiperazin-1-yl)quinolin-3-yl]carbamate → 3-Amino-N-{4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}-7-(3-oxopiperazin-1-yl)quinoline-2-carboxamide

HRID 924490Notes

Reaction equation

HRID 924490 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][C:16]([C:18]2[C:27]([NH:28]C(=O)OCC3C=CC=CC=3)=[CH:26][C:25]3[C:20](=[CH:21][C:22]([N:39]4[CH2:44][CH2:43][NH:42][C:41](=[O:45])[CH2:40]4)=[CH:23][CH:24]=3)[N:19]=2)=[O:17])[CH2:3]1.[H][H]>CO.[Pd]>[NH2:28][C:27]1[C:18]([C:16]([NH:15][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[N:4]2[CH2:5][C@H:6]([CH3:8])[CH2:7][C@H:2]([NH2:1])[CH2:3]2)=[O:17])=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[C:22]([N:39]1[CH2:44][CH2:43][NH:42][C:41](=[O:45])[CH2:40]1)[CH:21]=2

Participants

5

Reactant 2

HCID 86726934Benzyl [2-[({4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(3-oxopiperazin-1-yl)quinolin-3-yl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 867269353-Amino-N-{4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}-7-(3-oxopiperazin-1-yl)quinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl [2-[({4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(3-oxopiperazin-1-yl)quinolin-3-yl]carbamate (0.0086 g, 0.014 mmol) in 3.0 mL of MeOH was hydrogenated in the presence of 8 mg of 10% Pd on carbon under a balloon of hydrogen at room temperature for 1 h. The 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 C25H31N8O2 [M+H]+: m/z=475.3. found: 475.4.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by preparative HPLC (XBridge™ C18 column
  3. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-58110c143fab4b1ba89e9d759d8457b2
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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