Hydrochloric Acid → 6-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

HRID 1882132Notes

Reaction equation

HRID 1882132 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([O:26]CC)=[O:25])[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1.O[Li].O.Cl>C1COCC1.O>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([OH:26])=[O:25])[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67549791Ethyl 6-{(e)-2-[2-(cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylate

Product 1

HCID 593698916-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Step 4 intermediate (495 mg, 1.242 mmol) in THF (10 ml) was added LiOH.H2O (105 mg, 2.484 mmol) dissolved in water (10 ml). The mixture was stirred for 2 h at room temperature. Solvent was evaporated under reduced pressure and the residue obtained was acidified with 1 N HCl to pH 4 and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with water (2×25 mL) and dried (Na2SO4). Evaporation of solvent under reduced pressure afforded 0.381 g of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.26-0.28 (m, 2H), 0.49-0.53 (m, 2H), 1.16-1.22 (m, 1H), 3.75 (d, J=7.5 Hz, 2H), 3.79 (s, 3H), 6.95-6.99 (m, 1H), 7.04 (t, J=7.8 Hz, 1H), 7.16-7.27 (m, 1H), 7.39 (d, J=3.9 Hz, 1H), 7.71 (d, J=15.9 Hz, 1H), 7.79 (d, J=15.9 Hz, 1H), 8.10 (d, J=3.9 Hz, 1H), 13.44 (br s, 1H); ESI-MS (m/z) 369.08 (M−H)−.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue obtained
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined ethyl acetate extracts were washed with water (2×25 mL)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-a08e7e7b0ef24ad7a5bdc7b600470b87
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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