Ammonium formate → Ammonia

HRID 2383367Notes

Reaction equation

HRID 2383367 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:58][Si:59]([C:62]([CH3:65])([CH3:64])[CH3:63])([CH3:61])[CH3:60])[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH:35]([CH2:38][N:39]3[CH:43]=[N:42][C:41]([C@:44]([CH:52]4[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]4)([OH:51])[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[N:40]3)[CH2:34][CH2:33]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:17].[Si:59]([O:58][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38][N:39]2[CH:43]=[N:42][C:41]([C@:44]([CH:52]3[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)([OH:51])[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[N:40]2)[CH2:34][CH2:33]1)([C:62]([CH3:64])([CH3:65])[CH3:63])([CH3:61])[CH3:60]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 591459498-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}amino)ethyl]quinolin-2(1H)-one

Product 2

HCID 222AmmoniaHCID 591459695-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}amino)ethyl]-8-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

8-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({9-[4-({3-[(R)-cyclohexyl(hydroxy)phenylmethyl]-1H-1,2,4-triazol-1-yl}methyl)piperidin-1-yl]nonyl}amino)ethyl]quinolin-2(1H)-one (Preparation 7, 230 mg, 0.255 mmol) was dissolved in ethanol (10 ml) and palladium hydroxide [20 wt. % (dry basis) on carbon (wet)] (5 mg) added followed by ammonium formate (161 mg, 2.55 mmol). After stirring at reflux for 1 hour the reaction mixture was filtered through Arbocelt® and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97.5:2.5:0.25 to 90:10:1, by volume) to furnish the title compound as a glass, in 87% yield, 180 mg.

Workup

  1. temperatureat reflux for 1 hour the reaction mixture
  2. filtrationwas filtered through Arbocelt®
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3d4f6921355d4e5990da35aa9b782f7a
Source dataset
uspto-grants-2012_09
Patent number
US08263623B2

Reaction notes

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