Triethylamine → 3-[5-(4-Ethyl-thiazol-2-yl)-pyridin-2-yloxy]-propan-1-ol

HRID 734433Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[S:11])=[CH:8][N:7]=1.Br[CH2:16][C:17](=O)[CH2:18][CH3:19].C(N(CC)CC)C>CCO>[CH2:18]([C:17]1[N:12]=[C:10]([C:9]2[CH:13]=[CH:14][C:6]([O:5][CH2:4][CH2:3][CH2:2][OH:1])=[N:7][CH:8]=2)[S:11][CH:16]=1)[CH3:19]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-(3-hydroxy-propoxy)-thionicotinamide (Example 72, 8.8 g, 41.46 mmol) in EtOH (205 mL) at rt was added 1-bromo-2-butanone. The reaction mixture was then heated at 70° C. for 3 h. Upon completion, triethylamine was added and the volatiles were removed under reduced pressure. The crude material was suspended in CH2Cl2 and purified by flash chromatography. The column was eluted with a mixture of EtOAc/hexanes (30 to 50% EtOAc) to give the title compound as a white solid (10.04 g, 91%) after concentration of the chromatography fractions. 1H NMR (400 MHz, acetone-d6) δ 8.70 (s, 1H), 8.19 (dd, 1H), 7.15 (s, 1H), 6.86 (d, 1H), 4.48 (t, 2H), 3.74-3.71 (m, 3H), 2.83 (q, 2H), 2.01-1.98 (m, 2H), 1.32 (t, 3H). LC/MS m/z 265.3 (M+H)+; RT 2.12 min.

Workup

customthe volatiles were removed under reduced pressure
custompurified by flash chromatography
washThe column was eluted with a mixture of EtOAc/hexanes (30 to 50% EtOAc)

Sources & evidence

ORD record: ord-850211d860524cf6a9d4f6f5b6be1da1
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592361B2

Reaction notes

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