4-Toluenesulfonyl chloride → 4-Chloro-2-ethyl-1-{[5-(2-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-1H-benzimidazole-5-carbonitrile

HRID 913575Notes

Reaction equation

HRID 913575 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[N:7]([CH2:13][C:14]([OH:16])=O)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:17]#[N:18].CCN=C=NCCCN(C)C.Cl.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([NH:39][NH2:40])=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(#N)C.C1COCC1>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[N:7]([CH2:13][C:14]3[O:16][C:37]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=4)=[N:39][N:40]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:17]#[N:18]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 255881PicolinohydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67404468(4-Chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetic acid

Product 1

HCID 674049874-Chloro-2-ethyl-1-{[5-(2-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-1H-benzimidazole-5-carbonitrileYield 16.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4-Chloro-5-cyano-2-ethyl-1H-benzimidazol-1-yl)acetic acid (0.017 g, 0.065 mmol) and EDCl (0.014 mg, 0.072 mmol) were combined in acetonitrile (3 mL) and stirred at rt for 3 min. 2-Pyridinecarbohydrazide (0.0094 g, 0.068 mmol) was added next and the resulting mixture was stirred for 60 min. To this solution was added THF (THF 3 mL) followed by tosyl chloride (0.015 g, 0.078 mmol) and P-BEMP (0.148 g, 0.325 mmol, 2.2 mmol/g resin load). The reaction vessel was sealed and heated to 100° C. in a microwave for 5 min. The resin was filtered away and washed with CH2Cl2 (×2). The concentrated filtrate was purified (SiO2, 25% EtOAc/hexanes) to afford the title compound (0.004 g): MS (APCl) m/z 365 (M+1).

Workup

  1. stirringthe resulting mixture was stirred for 60 min
  2. customThe reaction vessel was sealed
  3. temperatureheated to 100° C. in a microwave for 5 min
  4. filtrationThe resin was filtered away
  5. washwashed with CH2Cl2 (×2)
  6. customThe concentrated filtrate was purified (SiO2, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b6f1e7a83f6643b69a7dd1dc1c62c082
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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