Reaction equation
Cl.[NH2:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9].Cl[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=1>>[NH2:2][C:3]1[N:7]([CH2:12][C:13]2[CH:14]=[C:15]([C:23]([F:25])([F:26])[F:24])[CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=2)[CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[O:9]Participants
Procedure
Wash sodium hydride (2.71 g of a 60% solution in mineral oil, 67.66 mmol) three times with hexanes, then dilute with 85 mL of DMF. To this mixture add the HCl salt of 5-amino-1H-imidazole-4-carboxylic acid amide (5.0 g, 30.75 mmol) neat in four portions. The mixture generates gas and remains cloudy and turns a slightly green color. After mixing for 40 min., add 1-chloromethyl-3,5-bis-trifluoromethyl-benzene (8.88 g, 33.83 mmol). (The mixture again generates gas and darkens). Stir at RT for 2 days, then pour through a plug of Celite and wash with DMF (50 mL) and xylenes (50 mL). Remove the DMF via azeotropic distillation with xylenes under reduced pressure (5×50 mL), and then concentrate the residue under a steady stream of nitrogen for 18 h to provide the title compound as a dark purple solid. MS (ES) 351.1, 353.1 (M+1); 1H NMR (300 MHz, CDCl3) δ 7.70 (s, 1H), 7.58 (s, 2H), 7.31 (s, 2H), 6.96 (s, 1H), 5.46 (s, 2H), 5.10 (s, 2H).
Workup
- washWash sodium hydride (2.71 g of a 60% solution in mineral oil, 67.66 mmol) three times with hexanes
- additiondilute with 85 mL of DMF
- additionAfter mixing for 40 min.
- additionpour through a plug of Celite
- washwash with DMF (50 mL) and xylenes (50 mL)
- customRemove the DMF
- distillationvia azeotropic distillation with xylenes under reduced pressure (5×50 mL)
- concentrationconcentrate the residue under a steady stream of nitrogen for 18 h
Sources & evidence
- ORD record
- ord-dd73dd882f0340b5a9de6a3b90c3a478
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179804B2
Linked notes
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