Hydrochloric Acid → HCID 44479585, compound

HRID 538136Notes

Reaction equation

HRID 538136 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]([Cl:27])[C:18]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:19][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.Cl.O>C(O)(=O)C>[Cl:27][C:17]1[C:18]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:19][C:13]2[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)[NH:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 66937474HCID 66937474, compound

Product 1

HCID 44479585HCID 44479585, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(6-Chloro-5-phenoxy-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.361 g) was dissolved in glacial acetic acid (9 mL) and 6N HCl (9 mL) and heated in a sealed tube at 100° C. for 6 h. After cooling in ice, water (5 mL) was added and the solids were collected via filtration, washed with water, and dried under vacuum (60° C., 10 mmHg). The resulting tan powder was recrystallized from MeOH:water (10 mL, 10:1), collected via filtration and dried under reduced pressure to afford the title compound as a tan solid (115 mg, 90%). Mp=134-138° C. (dec.). MS (ESI/CI): mass calcd. for C17H11ClN4O3, 354; m/z found, 355 [M+H]+, 396 [MH+MeCN]+. 1H NMR (mixture of tautomers) (500 MHz, DMSO-d6): 13.60 (s, 0.5H), 13.50 (s, 0.5H), 12.93 (s, 1H), 8.89 (s, 1H), 8.30 (s, 1H), 7.90 (s, 0.5H), 7.65 (s, 0.5H), 7.42 (m, 2.5H), 7.15 (m, 1.5H), 7.02-6.75 (m, 2H).

Workup

  1. temperatureAfter cooling in ice
  2. filtrationthe solids were collected via filtration
  3. washwashed with water
  4. customdried under vacuum (60° C., 10 mmHg)
  5. customThe resulting tan powder was recrystallized from MeOH
  6. filtrationwater (10 mL, 10:1), collected via filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7c277d0f3acb4df8b15486d63e09eebe
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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