Cyanogen Bromide → HCID 58542063, compound

HRID 1966737Notes

Reaction equation

HRID 1966737 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:30]=[CH:29][C:11]3[N:12]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:13]([C:15]4[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=4[C:17]([NH:19][NH2:20])=[O:18])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[N:36]#[C:37]Br>O1CCOCC1.O>[NH2:36][C:37]1[O:18][C:17]([C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=2[C:13]2[N:12]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:11]3[CH:29]=[CH:30][C:8]([C:5]4[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=4)=[CH:9][C:10]=3[N:14]=2)=[N:19][N:20]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58541884HCID 58541884, compound

Product 1

HCID 58542063HCID 58542063, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a vial is added 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-benzoic acid hydrazide (43 mg, 0.107 mmol) in 1,4-dioxane (2 mL), followed by the addition of NaHCO3 (13 mg, 0.155 mmol) in water (0.5 mL), then cyanogen bromide (13 mg, 0.123 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated in vacuo. The residue is loaded to a silica gel column. The column is eluted with 0-8% 2M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (30 mg, 66%) as an off-white solid. LCMS (ESMS): m/z 427.76 (M++1)

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washThe column is eluted with 0-8% 2M NH3 in MeOH/CH2Cl2
  3. customThe product fractions are collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c280108b3d744da1a4e22fcf2561c6df
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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