Hydrazine → HCID 58541884, compound

HRID 1966736Notes

Reaction equation

HRID 1966736 reaction equation
CO[C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]2[CH:19]=[CH:20][C:21]([C:23]3[CH:24]=[N:25][C:26]([NH2:29])=[N:27][CH:28]=3)=[CH:22][C:12]=2[N:11]=1.[NH2:31][NH2:32]>CCO>[NH2:29][C:26]1[N:25]=[CH:24][C:23]([C:21]2[CH:20]=[CH:19][C:13]3[N:14]([C:15]([CH3:17])([CH3:18])[CH3:16])[C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([NH:31][NH2:32])=[O:30])=[N:11][C:12]=3[CH:22]=2)=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57329419HCID 57329419, compound

Product 1

HCID 58541884HCID 58541884, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a vial is added 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-benzoic acid methyl ester (example 16) (85 mg, 0.212 mmol) in EtOH (5 mL), follow by the addition of hydrazine (35 wt % solution in water) (1 mL). The reaction mixture is stirred at 80° C. for 5 days. The reaction mixture is concentrated in vacuo. The residue is loaded to a silica gel column. The column is eluted with 0-10% 2M NH3 in MeOH/CH2Cl2. The product fractions are collected and is concentrated to afford 2-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-benzoic acid hydrazide (43 mg, 51%) as a off-white solid. LCMS (ESMS): m/z 402.57 (M++1)

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washThe column is eluted with 0-10% 2M NH3 in MeOH/CH2Cl2
  3. customThe product fractions are collected
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-809f75015b084f748f5a631156f1e049
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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