Cyanogen Bromide → HCID 178493860, compound

HRID 536231Notes

Reaction equation

HRID 536231 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 (Step 4, 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-5954a1c1f37d43b19175977a65f5f9d7
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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