Formamidine acetate → HCID 178432631, compound

HRID 1907195Notes

Reaction equation

FC(F)(F)C(O)=O.[Br:8][C:9]1[N:13]([CH3:14])[N:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]([CH3:21])[N:18]([NH2:20])[CH:19]=1.C(O)(=O)C.[CH:26](N)=[NH:27]>CC(O)CC>[Br:8][C:9]1[N:13]([CH3:14])[N:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]([CH3:21])[N:18]([NH:20][CH:26]=[NH:27])[CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-(5-Bromo-1-methyl-1H-pyrazol-4-yl)-2-methyl-1H-imidazol-1-amine, trifluoroacetate salt (4.90 g, 113.2 mmol) was combined with formamidine acetate (98%, 4.92 g, 46.3 mmol) in 2-butanol (40 mL), and the reaction mixture was heated at 100° C. for 6 hours, then allowed to cool to room temperature and stir for 18 hours. The off-white solid was collected by filtration and washed with 2-propanol followed by diethyl ether. The solid was then triturated with aqueous ammonium hydroxide (7.5 M, 40 mL); filtration provided a white solid, which was washed with 2-propanol followed by diethyl ether to provide the product. Yield: 2.70 g, 9.54 mmol, 72%. 1H NMR (500 MHz, CD3OD), presumed to be a mixture of rotamers or tautomers: δ 2.26 and 2.31 (2 s, 3H), 3.89 and 3.89 (2 s, 3H), 7.26 and 7.40 (2 s, 1H), 7.41 and 7.96 (2 br s, 1H), 7.85 and 7.82 (2 s, 1H).

Workup

temperatureto cool to room temperature
filtrationThe off-white solid was collected by filtration
washwashed with 2-propanol
customThe solid was then triturated with aqueous ammonium hydroxide (7.5 M, 40 mL)
filtrationfiltration
customprovided a white solid, which
washwas washed with 2-propanol
customto provide the product
additiona mixture of rotamers or tautomers
customδ 2.26 and 2.31 (2 s, 3H), 3.89 and 3.89 (2 s, 3H), 7.26 and 7.40 (2 s, 1H), 7.41 and 7.96 (2 br s, 1H), 7.85 and 7.82 (2 s, 1H)

Sources & evidence

ORD record: ord-7fd1be415d40403887c1bf8ad874eee3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598155B2

Reaction notes

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