Pyridine → HCID 88363012, compound

HRID 2284164Notes

Reaction equation

HRID 2284164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]3[CH:14]=[C:15]([NH:18][C:19]([C:21]4[CH:30]=[CH:29][C:24]([C:25](OC)=[O:26])=[CH:23][CH:22]=4)=[O:20])[CH:16]=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.CO[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[NH:43]C3C=C(N)C=CC=3N=2)=[CH:35][CH:34]=1.ClC(C1C=CC(C([O:58][CH3:59])=O)=CC=1)=O.[N:62]1C=CC=CC=1>>[CH3:59][O:58][C:38]1[CH:37]=[C:36]([CH:35]=[CH:34][CH:33]=1)/[CH:39]=[N:43]/[NH:62][C:25]([C:24]1[CH:23]=[CH:22][C:21]([C:19]([NH:18][C:15]2[CH:16]=[CH:17][C:11]3[N:10]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[NH:13][C:12]=3[CH:14]=2)=[O:20])=[CH:30][CH:29]=1)=[O:26]

Participants

5

Reactant 4

HCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 8955532-(4-Methoxyphenyl)-1H-benzimidazol-6-amineHCID 44215117HCID 44215117, compound

Product 1

HCID 88363012HCID 88363012, compoundYield 44%

Procedure

Compound 269 was prepared according to the general procedure described in Scheme V. Preparation of methyl 4-((2-(4-methoxyphenyl)-1H-benzo[d]imidazol-6-yl)carbamoyl)benzoate: 2-(4-Methoxyphenyl)-1H-benzo[d]imidazol-6-amine (120 mg, 0.5 mmol) and methyl 4-(chlorocarbonyl)benzoate (80 mg, 0.4 mmole) were place in a 20 mL vial and pyridine (2.0 mL) added and capped tightly. The reaction mixture was stirred at room temperature for 2 h till a solid precipitated out. To this mixture, 10 mL EtOAC was added and stirred for further 15 minutes then filtered. The filter cake was washed with plenty of water and then with some EtOAc (10 mL) and dried to provide pure title compound (70 mg, 44% yield).

Workup

  1. customCompound 269 was prepared
  2. customcapped tightly
  3. customprecipitated out
  4. additionTo this mixture, 10 mL EtOAC was added
  5. stirringstirred for further 15 minutes
  6. filtrationthen filtered
  7. washThe filter cake was washed with plenty of water
  8. dry with materialwith some EtOAc (10 mL) and dried

Sources & evidence

ORD record
ord-90e365f0f4d1452884fae6678ba42a08
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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