HCID 86619471, compound → HCID 59703213, compound

HRID 1365598Notes

Reaction equation

HRID 1365598 reaction equation
[OH2:1].[PH2]([O-])=O.C([NH+](CC)CC)C.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]#N)[CH:16]=[CH:15][C:14]=1[N:21]1[C:25]2[C:26]3[S:30][C:29]([NH:31][C:32](=[O:34])[CH3:33])=[N:28][C:27]=3[CH2:35][CH2:36][C:24]=2[C:23]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[N:22]1>[Ni].ClCCl.CO>[Cl:12][C:13]1[CH:18]=[C:17]([CH:19]=[O:1])[CH:16]=[CH:15][C:14]=1[N:21]1[C:25]2[C:26]3[S:30][C:29]([NH:31][C:32](=[O:34])[CH3:33])=[N:28][C:27]=3[CH2:35][CH2:36][C:24]=2[C:23]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)=[N:22]1

Participants

6

Reactant 2

HCID 86619471HCID 86619471, compoundHCID 178465534HCID 178465534, compound

Product 1

HCID 59703213HCID 59703213, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

In a hydrogenation reactor under an argon atmosphere, triethylammonium hypophosphite hydrate (2.2 mL, 12 mmol) is added at 10° C. to a suspension of Raney nickel (8 g, 93 mmol) in 75 mL dichloromethane and 75 mL methanol. After the release of gas has died away N-[1-(2-chloro-4-cyanophenyl)-3-pyridin-3-yl-4,5-dihydro-1H-pyrazolo[4,3-g]benzothiazol-7-yl]-acetamide (PCT/EP05055021) (2.7 g, 5.6 mmol) is added and the mixture is stirred for 3 h at 55° C. The reaction mixture is filtered and the filtrate is evaporated down. The residue is purified on silica gel with dichloromethane/methanol.

Workup

  1. additionis added
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated down
  4. customThe residue is purified on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-2bf34c0e875a43ddb48267695653f24c
Source dataset
uspto-grants-2011_02
Patent number
US07893049B2

Reaction notes

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