Hydrochloric Acid → HCID 58564281, compound

HRID 1753974Notes

Reaction equation

HRID 1753974 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[N:10]=[N:9][C:8]([C:11]2[S:15][C:14]([N:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)=[N:13][CH:12]=2)=[N:7]1)[CH3:2].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[N:10]=[N:9][C:8]([C:11]2[S:15][C:14]([N:16]3[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]3)=[N:13][CH:12]=2)=[N:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733664HCID 131733664, compound

Product 1

HCID 58564281HCID 58564281, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl{5-[2-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-1,3-thiazol-5-yl]-2H-tetrazol-2-yl}acetate (377 mg, 0.99 mmol) in THF (4.95 mL) was added 1N HCl (1.09 mL, 1.09 mmol). The reaction mixture was heated to 65° C. for 3 h. The volatiles were evaporated under reduced pressure. The mixture was diluted with water (20 mL) and extracted with EtOAc (3×5 mL). The combined organic fractions were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by Combiflash™ chromatography (SiO2, 12 g, elution with 10-70% EtOAc/hexanes over 40 min) to afford the title compound as solid. 1H NMR (500 MHz, DMSO-d6): δ 7.92 (s, 1 H), 5.85 (s, 2 H), 4.22 (q, 2 H), 3.90 (t, 4 H), 2.57 (t, 4 H), 1.23 (t, 3 H). MS (+ESI): m/z 337.1 (MH+).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. additionThe mixture was diluted with water (20 mL)
  3. extractionextracted with EtOAc (3×5 mL)
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by Combiflash™ chromatography (SiO2, 12 g, elution with 10-70% EtOAc/hexanes over 40 min)

Sources & evidence

ORD record
ord-5c9b86d4b592430181a29be0351feaa6
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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