Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate → tert-butyl [(3S,5R)-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-(trifluoromethyl)piperidin-3-yl]carbamate

HRID 924480Notes

Reaction equation

HRID 924480 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[CH2:12][N:11]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[C:37]([NH:38]C(=O)OCC3C=CC=CC=3)=[CH:36][C:35]3[C:30](=[CH:31][C:32]([C:49]4[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH:54]=4)=[CH:33][CH:34]=3)[N:29]=2)=[O:27])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:38][C:37]1[C:28]([C:26]([NH:25][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:19]=2[N:11]2[CH2:12][C@H:13]([C:15]([F:18])([F:16])[F:17])[CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]2)=[O:27])=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[C:32]([CH:49]1[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]1)[CH:31]=2

Participants

5

Reactant 2

HCID 86726924Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86726925tert-butyl [(3S,5R)-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-(trifluoromethyl)piperidin-3-yl]carbamateYield 79.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)quinolin-3-yl]carbamate (0.010 g, 0.013 mmol) in 1.5 mL of MeOH was hydrogenated in the presence of 10% Pd on carbon (3.5 mg) under a balloon of hydrogen at room temperature for 1 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to give tert-butyl [(3S,5R)-1-[3-({[3-amino-7-(1-methylpiperidin-4-yl)quinolin-2-yl]carbonyl}amino)pyridin-4-yl]-5-(trifluoromethyl)piperidin-3-yl]carbamate (0.0065 g, 79%). LCMS calc. for C32H41F3N7O3 [M+H]+: m/z=628.3. found: 628.3.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d51d0c6d35aa47e38fb6711fbf0d73be
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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