Ammonium formate → HCID 131734221, compound

HRID 1497660Notes

Reaction equation

HRID 1497660 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][C:19]([C:44]3[CH:49]=[CH:48][N:47]=[C:46]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH:45]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([S:32]([C:35]4[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=4[F:42])(=[O:34])=[O:33])[CH2:29][O:30][CH3:31])[C:23]=3[F:43])[N:21]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:54]([O:53][C:51](=[O:52])[NH:50][C:46]1[CH:45]=[C:44]([C:19]2[S:18][C:17]([CH:14]3[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)=[N:21][C:20]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([S:32]([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])(=[O:33])=[O:34])[CH2:29][O:30][CH3:31])[C:23]=2[F:43])[CH:49]=[CH:48][N:47]=1)([CH3:57])([CH3:55])[CH3:56]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68285114HCID 68285114, compound

Product 1

HCID 131734221HCID 131734221, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl-4-[5-{2-[(tert-butoxycarbonyl)amino]pyridin-4-yl}-4-(3-{[(2,5-difluorophenyl)sulfonyl]-(methoxymethyl)amino}-2-fluorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (prepared as described in Example 10, 110 mg, 0.13 mmol) was dissolved in absolute ethanol (10 mL) under nitrogen atmosphere. Ammonium formate (440 mg, 7 mmol) and palladium on charcoal 5% (150 mg portionwise) were then added. The mixture was refluxed for 2 days, then filtered on a celite pad and evaporated to dryness. The residue was taken up with DCM and washed with water. The organic layer was dried over Na2SO4 and evaporated, affording 75 mg (84%) of tert-butyl-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl]-(methoxymethyl)amino}-2-fluorophenyl)-2-(piperidin-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}carbamate.

Workup

  1. temperatureThe mixture was refluxed for 2 days
  2. filtrationfiltered on a celite pad
  3. customevaporated to dryness
  4. washwashed with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-468ae7565f884387b4e2045acbf592e1
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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