Ammonium formate → HCID 136358401, compound

HRID 601305Notes

Reaction equation

HRID 601305 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:35])[N:21]([NH:30][CH2:31][CH:32]4[CH2:34][CH2:33]4)[C:22]4[C:27]([C:28]=3[OH:29])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[Pd].[OH-].[OH-].[Pd+2]>[CH:32]1([CH2:31][NH:30][N:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:28]([OH:29])=[C:19]([C:14]3[NH:13][C:12]4[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][C:11]=4[S:16](=[O:17])(=[O:18])[N:15]=3)[C:20]2=[O:35])[CH2:33][CH2:34]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 1363584023-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-1-[(cyclopropylmethyl)amino]-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 136358401HCID 136358401, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 320B (0.296 g, 0.57 mmol) in tetrahyrofuran (15 mL) was reacted with a catalytic amount of palladium hydroxide on carbon, a catalytic amount of 5% palladium on carbon, and ammonium formate (0.180 g, 2.85 mmol) at 60° C. for 2 hours. The warm reaction mixture was filtered through celite® (diatomaceous earth) and the filtrate was diluted with diethyl ether and the precipitate filtered and dried to give the title compound (0.127 g, 53%).

Workup

  1. customThe warm reaction mixture
  2. filtrationwas filtered through celite® (diatomaceous earth)
  3. additionthe filtrate was diluted with diethyl ether
  4. filtrationthe precipitate filtered
  5. customdried

Sources & evidence

ORD record
ord-bb9973160b93467ba0e49d2aebe1d180
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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