Cyanogen Bromide → HCID 178493860, compound

HRID 1259515Notes

Reaction equation

HRID 1259515 reaction equation
[N:1]#[C:2]Br.[NH:4]1[CH2:8][CH2:7][N:6]=[C:5]1[C:9]1[C:14]([NH2:15])=[C:13]([O:16][CH3:17])[C:12]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:11][CH:10]=1>C(Cl)Cl>[CH3:17][O:16][C:13]1[C:14]2[N:15]=[C:2]([NH2:1])[N:4]3[CH2:8][CH2:7][N:6]=[C:5]3[C:9]=2[CH:10]=[CH:11][C:12]=1[O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 582198516-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxy-3-(3-morpholin-4-ylpropoxy)aniline

Product 1

HCID 178493860HCID 178493860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanogen bromide (10.9 g, 102.9 mmol) was added to a mixture of 6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxy-3-(3-morpholin-4-ylpropoxy)aniline (17.2 g, 51.4 mmol) and TEA (15.6 g, 154.3 mmol) in DCM (200 mL) precooled to 0° C. After 1 h the reaction mixture was concentrated under reduced pressure and the resulting residue stirred with EtOAc (300 mL) overnight at rt. The resulting slurry was filtered to generate the title compound contaminated with triethylamine hydrobromide (26.2 g, 71%): HPLC MS RT=0.17 min, MH+=360.2.

Workup

  1. customprecooled to 0° C
  2. concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
  3. filtrationThe resulting slurry was filtered

Sources & evidence

ORD record
ord-1455c20d537f4905be009f441660ee98
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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