Hydrochloric Acid → 2-(4-((2-Bromoethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

HRID 2065861Notes

Reaction equation

HRID 2065861 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH:4]1[CH2:8][S:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[N:5]1.[Br:21][CH2:22]CO.Cl.C([O-])(=O)C.C([NH+](CC)CC)C>O1CCOCC1>[Br:21][CH2:22][CH2:20][O:19][CH:3]([O:2][CH3:1])[CH:4]1[CH2:8][S:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[N:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 11073729Triethyl ammonium acetateHCID 1361941002-(4-(Dimethoxymethyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

Product 1

HCID 1358628842-(4-((2-Bromoethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a vial containing 2-(4-(dimethoxymethyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol (50 mg), 2-bromoethanol (1 mL) and a solution of HCl in dioxane (125 uL of 4M) was added. After 4 hours at room temperature, an aqueous solution of triethylammonium acetate (TEAA) (1 mL of 1M) was added to the reaction. After filtration, the solution was purified by preparative RP-HPLC by eluting with 50 mM TEAA ramping to acetonitrile over 30 min. Yield 26 mg. 1H NMR (300 MHz, CDCl3) δ 7.96 (d, J=8.9, 1H), 7.33 (d, J=2.4, 1H), 7.06 (dd, J=2.3, 8.9, 1H), 4.88 (dt, J=6.8, 13.2, 1H), 4.79-4.67 (m, 1H), 4.16-3.73 (m, 3H), 3.64-3.38 (m, 8H), 1.36 (dd, J=2.4, 5.3, 1H). mass spectrum, calculated (MH+) 304/306. found 304/306

Workup

  1. filtrationAfter filtration
  2. customthe solution was purified by preparative RP-HPLC
  3. washby eluting with 50 mM TEAA ramping to acetonitrile over 30 min

Sources & evidence

ORD record
ord-ea095ff5c0b843f695b89928a3ba956c
Source dataset
uspto-grants-2012_10
Patent number
US08288559B2

Reaction notes

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