Ammonium formate → Jtk-853

HRID 908627Notes

Reaction equation

HRID 908627 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[O:44][C:45]([F:48])([F:47])[F:46])[CH2:5][NH:6][C:7]([C@H:9]1[CH2:14][N:13]([C:15]2[S:16][C:17]3[C:22](Cl)=[N:21][C:20]([CH:24]4[CH2:26][CH2:25]4)=[N:19][C:18]=3[N:27]=2)[CH2:12][CH2:11][N:10]1[S:28]([C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=1)(=[O:30])=[O:29])=[O:8].C([O-])=O.[NH4+]>C(O)C.C(OCC)(=O)C.[C].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[O:44][C:45]([F:48])([F:46])[F:47])[CH2:5][NH:6][C:7]([C@H:9]1[CH2:14][N:13]([C:15]2[S:16][C:17]3[CH:22]=[N:21][C:20]([CH:24]4[CH2:26][CH2:25]4)=[N:19][C:18]=3[N:27]=2)[CH2:12][CH2:11][N:10]1[S:28]([C:31]1[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:40])[F:39])=[CH:35][CH:36]=1)(=[O:30])=[O:29])=[O:8]

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 59703761(R)-4-(7-chloro-5-cyclopropyl-thiazolo[4,5-d]pyrimidin-2-yl)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 3-fluoro-4-trifluoromethoxy-benzylamide

Product 1

HCID 57519700Jtk-853Yield 62.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst4×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of the compound (49 mg) obtained in Step 6 and ammonium formate (42 mg) in ethanol (1.0 ml) was added 10% palladium carbon (25 mg) at 80° C. After stirring at 80° C. for 30 min, 10% palladium carbon (25 mg) was added. After stirring at 80° C. for 30 min, ammonium formate (42 mg) and 10% palladium carbon (25 mg) were added. After stirring at 80° C. for 30 min, 10% palladium carbon (25 mg) was added. After stirring at 80° C. for 30 min, the reaction mixture was allowed to return to room temperature, and the reaction mixture was diluted with ethyl acetate. The mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (methanol:chloroform=1:10) to give the title compound (29 mg).

Workup

  1. stirringAfter stirring at 80° C. for 30 min
  2. stirringAfter stirring at 80° C. for 30 min
  3. stirringAfter stirring at 80° C. for 30 min
  4. customto return to room temperature
  5. filtrationThe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by thin layer silica gel chromatography (methanol:chloroform=1:10)

Sources & evidence

ORD record
ord-1e8f19a3eaf44bee9b4e78aac27d7a60
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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