Tetrahydrofuran → HCID 178483007, compound
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([N:10]([CH3:12])[CH3:11])[N:7](C(OC(C)(C)C)=O)[C:6]=2[CH:20]=1.BrC1C=C[C:25]2[N:29]=[C:28](N(C)C)[NH:27][C:26]=2C=1.C(OC(OC(C)(C)C)=O)([O:36][C:37](C)(C)[CH3:38])=O.C(N(CC)CC)C.C[N:57]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][N:60]=1)[CH3:58].[O:65]1CCCC1>>[CH3:12][N:10]([CH3:11])[C:8]1[NH:9][C:5]2[CH:4]=[CH:3][C:2]([C:26]3[N:27]=[C:28]4[N:60]([CH2:61][CH:62]5[CH2:63][CH2:64][O:36][CH2:37][CH2:38]5)[C:59](=[O:65])[NH:57][C:58]4=[N:29][CH:25]=3)=[CH:20][C:6]=2[N:7]=1Participants
7
Procedure
tert-Butyl 6-bromo-2-(dimethylamino)-1H-benzo[d]imidazole-1-carboxylate. A solution of 6-bromo-N,N-dimethyl-1H-benzo[d]imidazol-2-amine (0.5 g, 2.08 mmol), di-tert-butyl dicarbonate (0.54 g, 2.5 mmol), triethylamine (0.35 mL, 2.55 mmol) and dimethylaminopyridine (few crystals) in anhydrous tetrahydrofuran (10 mL) was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes) to provide the desired product (0.32 g, 54%) as a white solid. MS (ESI) m/z 341.3 [M+1]+.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe crude product was purified by Biotage chromatography (0-55% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-419f85ebb60e4f729c7304ed577cde50
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372976B2
Reaction notes
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