Dimethylformamide → 2-(4-((2-(Dimethylamino)ethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

HRID 2065862Notes

Reaction equation

HRID 2065862 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]([O:21][CH3:22])[CH:6]1[CH2:10][S:9][C:8]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[N:7]1.[CH3:23][N:24](C=O)[CH3:25]>>[CH3:23][N:24]([CH3:25])[CH2:2][CH2:3][O:4][CH:5]([O:21][CH3:22])[CH:6]1[CH2:10][S:9][C:8]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[N:15]=2)=[N:7]1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 1358628842-(4-((2-Bromoethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

Product 1

HCID 1361941052-(4-((2-(Dimethylamino)ethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol

Procedure

To a vial containing 2-(4-((2-bromoethoxy)(methoxy)methyl)-4,5-dihydrothiazol-2-yl)benzo[d]thiazol-6-ol (16 mg) in DMF (200 uL) dimethylamine (40 uL of 2M in THF) was added. After 28 hours at room temperature, the reaction was purified by preparative RP-HPLC to yield 8 mg. 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=9.2, 1H), 7.14 (d, J=2.2, 1H), 6.97 (d, J=8.9, 1H), 4.74-4.59 (m, 2H), 4.12-3.78 (m, 1H), 3.21 (dd, J=7.2, 14.9, 1H), 3.10 (s, 2H), 2.63 (s, 5H), 1.29 (t, J=7.3, 1H). mass (MH+) calc and found 368.

Workup

  1. additionwas added
  2. customthe reaction was purified by preparative RP-HPLC
  3. customto yield 8 mg

Sources & evidence

ORD record
ord-bc75485b8d5f4201ada93a5f874f91f2
Source dataset
uspto-grants-2012_10
Patent number
US08288559B2

Reaction notes

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