Hydrochloric Acid → HCID 66937397, compound

HRID 538144Notes

Reaction equation

HRID 538144 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[N:15](COCCOC)[C:14]3[CH:22]=[C:23]([Cl:34])[C:24]([S:26][C:27]4[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=4)=[CH:25][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])[CH3:2].CCO.Cl>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:22]=[C:23]([Cl:34])[C:24]([S:26][C:27]4[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=4)=[CH:25][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66937322HCID 66937322, compound

Product 1

HCID 66937397HCID 66937397, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 1-[6-chloro-1-(2-methoxy-ethoxymethyl)-5-m-tolylsulfanyl-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.190 g, 0.379 mmol) and EtOH (1 mL) was added 4M HCl in dioxane (1 mL). The mixture was stirred for 3 h at 23° C. The reaction mixture was concentrated and Et2O (10 mL) was added. The solids were filtered and washed with Et2O to yield the titled compound (0.143 g, 91%). MS (ESI/CI): mass calcd. for C20H17ClN4O2S, 412.1; m/z found, 413.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.95 (s, 1H), 8.35 (s, 1H), 7.77 (s, 1H), 7.41 (s, 1H), 7.29 (t, J=7.7 Hz, 1H), 7.19-7.14 (m, 2H), 7.12-7.06 (m, 1H), 4.30 (q, J=7.1 Hz, 2H), 2.29 (s, 3H), 1.31 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionEt2O (10 mL) was added
  3. filtrationThe solids were filtered
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-c3c5b8267add4400b4e041f2ac672301
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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