Formic Acid → HCID 59320268, compound

HRID 655281Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[C:19]([NH2:24])[C:20]([NH2:23])=[CH:21][CH:22]=4)=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:25](O)=O>>[N:23]1[C:20]2[CH:21]=[CH:22][C:17]([CH2:16][C:13]3[N:11]4[N:12]=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH:8]=[CH:9][C:10]4=[N:15][N:14]=3)=[CH:18][C:19]=2[NH:24][CH:25]=1

Participants

Reactant 2

HCID 284Formic Acid

HCID 59320427HCID 59320427, compound

Product 1

HCID 59320268HCID 59320268, compoundYield 73%

Conditions

Temperature: 100 °C

Procedure

A suspension of 4-(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-benzene-1,2-diamine (20 mg, 0.063 mmol) in formic acid (0.5 mL) was stirred at 100° C. for 5 h. The reaction mixture was cooled to room temperature and filtered through a 0.45 micron filter. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC on Xbridge prep C18 column (5 microns, 19×150 mm) using a formic acid buffered gradient of acetonitrile in water to return the title compound as an off-white solid (15 mg, 0.046 mmol, 73% yield). Analytical data presented in Table 1.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a 0.45 micron
filtrationfilter
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified by preparative HPLC on Xbridge prep C18 column (5 microns, 19×150 mm)

Sources & evidence

ORD record: ord-18c36f292cc74a2d8e8a7deaf9be0590
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071581B2

Reaction notes

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