Cyanogen Bromide → 5-chloro-1-(tetrahydro-pyran-4-ylmethyl)-1H-benzimidazol-2-ylamine

HRID 469724Notes

Reaction equation

HRID 469724 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:7]=1.[N:17]#[C:18]Br>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[C:18]([NH2:17])=[N:16][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 637259554-chloro-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,2-diamine

Product 1

HCID 552279795-chloro-1-(tetrahydro-pyran-4-ylmethyl)-1H-benzimidazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-N1-(tetrahydro-pyran-4-ylmethyl)-benzene-1,2-diamine (1.026 g; 4.261 mmol) is dissolved in ethanol (65 mL) and cyanogen bromide (0.903 g; 8.522 mmol) is added. The reaction is stirred at room temperature overnight. After this time the mixture is concentrated in vacuo to afford title compound as a tan solid which was used without further purification. ESI m/z 266 [M+H]+/264 [M−H]−

Workup

  1. concentrationAfter this time the mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-3923116476e1420eac7938d38431a599
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

Loading…