Acetic Anhydride → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-yl-methyl]-3-methyl-8-propyl-[1,2,4]triazolo[4,3-c]pyrimidine

HRID 916671Notes

Reaction equation

[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([NH:20][NH2:21])[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:25](OC(=O)C)(=O)[CH3:26].C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[C:25]([CH3:26])=[N:21][N:20]=[C:16]4[C:15]=3[CH2:22][CH2:23][CH3:24])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 131 (620 mg, 0.7 mmol) and acetic anhydride (2 mL) is stirred at 110° C. for one hour. NaHCO3 (aq.) (10 mL) and dichloromethane (10 mL) are added. The organic layer is separated and the aqueous layer is extracted with dichloromethane (2×10 mL). The combined organic layers are dried (NaSO4) and solvent removed. The crude product is separated by PTLC (5% methanol in dichloromethane) to yield 186; LC-MS, M+1 352.18; 1H-NMR (CDCl3) δ: 8.59 (s, 1H), 8.42 (d, 1H), 7.54 (t, 1H), 7.23–7.35 (m, 2H), 7.21 (s, 1H), 5.77 (s, 2H), 2.98 (t, 2H), 2.78 (s, 3H), 1.62–1.74 (m, 2H), 0.97 (t, 3H).

Workup

customThe organic layer is separated
extractionthe aqueous layer is extracted with dichloromethane (2×10 mL)
dry with materialThe combined organic layers are dried (NaSO4) and solvent
customremoved
customThe crude product is separated by PTLC (5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-9f164d9bfb0d4befb689a2444ef8eb38
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271170B2

Reaction notes

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