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

HRID 924478Notes

Reaction equation

HRID 924478 reaction equation
[NH2:1][C:2]1[C:3]([C:19]([NH:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[N:28]2[CH2:33][C@H:32]([CH3:34])[CH2:31][C@H:30]([NH:35]C(=O)OC(C)(C)C)[CH2:29]2)=[O:20])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[CH:6]=2.Cl>O1CCOCC1.CO>[NH2:1][C:2]1[C:3]([C:19]([NH:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[N:28]2[CH2:33][C@H:32]([CH3:34])[CH2:31][C@H:30]([NH2:35])[CH2:29]2)=[O:20])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[CH:6]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86726922tert-butyl {(3S,5R)-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidin-3-yl}carbamate

Product 1

HCID 867269233-Amino-N-{4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]pyridin-3-yl}-7-(1-methylpiperidin-4-yl)quinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To the intermediate tert-butyl {(3S,5R)-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-methylpiperidin-3-yl}carbamate, 1 mL of 4 M HCl in dioxane and 1 mL of MeOH were added. The mixture was stirred at room temperature for 1 h then concentrated under reduced pressure. The resulting residue was dissolved in 4.5 mL of MeOH and treated with 0.3 mL of NH4OH solution. 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 C27H36N7O [M+H]+: m/z=474.3. found: 474.4.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 4.5 mL of MeOH
  3. additiontreated with 0.3 mL of NH4OH solution
  4. filtrationThe mixture was filtered
  5. customthe filtrate was purified by preparative HPLC (XBridge™ C18 column
  6. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.)

Sources & evidence

ORD record
ord-dfad972433db4c77a0f88a5f271aa3be
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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