Hydrazine hydrate (1:1) → HCID 10183116, compound

HRID 8265Notes

Reaction equation

HRID 8265 reaction equation
O.NN.[CH3:4][N:5]([CH3:39])[C:6](=S)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([C:24]4[C:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)=[N:27][N:26]5[CH2:35][CH2:36][CH2:37][C:25]=45)=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[CH:8]=1>CO.[Ni]>[CH3:4][N:5]([CH3:39])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([C:24]4[C:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)=[N:27][N:26]5[CH2:35][CH2:36][CH2:37][C:25]=45)=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10206741HCID 10206741, compound

Product 1

HCID 10183116HCID 10183116, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a refluxing mixture of Raney-nickel and hydrazine-monohydrate (0.5 mL, 10.17 mmol) in methanol (5 mL) is added N,N-dimethyl-3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-thiobenzamide (311.0 mg, 0.63 mmol) in methanol (20 mL). The mixture is stirred 10 min and cooled to room temperature, filtered, and concentrated in vacuo. The residue is chromatographed by HPLC (C18 column) to yield the title compound, 60.2 mg (20%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue is chromatographed by HPLC (C18 column)

Sources & evidence

ORD record
ord-284abedd07c4462bb70a539a3f546733
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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