Dimethylformamide → HCID 59320427, compound

HRID 655215Notes

Reaction equation

HRID 655215 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH2:10][C:11]2[N:15]3[N:16]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[CH:19][C:14]3=[N:13][N:12]=2)[CH:7]=[CH:6][C:5]=1[NH2:26])([O-])=O.CN(C)C=O>CO.O1CCCC1.[Pd]>[C:20]1([C:17]2[CH:18]=[CH:19][C:14]3[N:15]([C:11]([CH2:10][C:8]4[CH:9]=[C:4]([NH2:1])[C:5]([NH2:26])=[CH:6][CH:7]=4)=[N:12][N:13]=3)[N:16]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 68702387HCID 68702387, compound

Product 1

HCID 59320427HCID 59320427, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-nitro-4-(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenylamine (89 mg, 0.257 mmol) and 10% wt Pd/C (27 mg, 0.026 mmol) in methanol (4 mL), tetrahydrofuran (2 mL), and dimethylformamide (2 mL) was stirred at room temperature under hydrogen atmosphere for 4 h. Catalyst was filtered through celite and the filtrate was concentrated and dried in vacuo to provide 81 mg of the product as a beige solid. 1HNMR (DMSO) δ 4.30 (s, 2H), 4.32 (s, 2H), 4.43 (s, 2H), 6.43 (m, 2H), 6.50 (s, 1H), 7.60 (m, 3H), 7.93 (d, 1H), 8.11 (m, 2H), 8.39 (d, 1H); MS (m/z) 317 [M+H+]+.

Workup

  1. filtrationCatalyst was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-374131d79745479fbf1dcc034b8971be
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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