17694-68-7 → HCID 9968105, compound

HRID 1796031Notes

Reaction equation

[Br-].Br[CH2:3][C:4]([C:6]1[CH:7]=[NH+:8][CH:9]=[CH:10][CH:11]=1)=O.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:19]=[CH:18][N:17]2[C:20]([C:23](=[S:25])[NH2:24])=[CH:21][N:22]=[C:16]2[N:15]=1>CN(C=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]2[N:24]=[C:23]([C:20]3[N:17]4[CH:18]=[CH:19][C:14]([C:13]([F:27])([F:26])[F:12])=[N:15][C:16]4=[N:22][CH:21]=3)[S:25][CH:3]=2)[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(Bromoacetyl)pyridinium bromide (41 mg, 0.14 mmol) was added to a stirred solution of the foregoing thioamide (24 mg, 0.1 mmol) in DMF (1 ml) at room temperature under N2. The reaction was warmed to 60° C. for 1 h and then concentrated under reduced pressure while azeotroping with xylene (20 ml). The crude residue was taken up in EtOAc (50 ml), washed with saturated sodium hydrogencarbonate solution (20 ml) and concentrated under reduced pressure while dry loading onto silica. Subsequent purification by column chromatography on silica using 70% EtOAc in hexanes containing 1% Et3N and 1% MeOH as the eluent gave 3-[4-(pyridin-3-yl)thiazol-2-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (33 mg, 97%): δH (400 MHz, d6-DMSO) 7.52-7.60 (1H, m), 7.80 (1H, d, J 7.1), 8.43 (1H, s), 8.50 (1H, dt, J 7.8 and 2.0), 8.62 (1H, m), 8.83 (1H, s), 9.39 (1H, s), 10.33 (1H, d, J 7.1); m/z (ES+) 347 (M+).

Workup

concentrationconcentrated under reduced pressure
customwhile azeotroping with xylene (20 ml)
washwashed with saturated sodium hydrogencarbonate solution (20 ml)
concentrationconcentrated under reduced pressure
customwhile dry loading onto silica
customSubsequent purification by column chromatography on silica using 70% EtOAc in hexanes containing 1% Et3N and 1% MeOH as the eluent

Sources & evidence

ORD record: ord-532300ffcc2044c687a85765b87696c8
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030128B2

Reaction notes

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