Morpholin-2-ylmethanol → {4-[4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzyl]morpholin-2-yl}methanol

HRID 547356Notes

Reaction equation

HRID 547356 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH:21]([CH2:25][OH:26])[CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:19]2[CH2:24][CH2:23][O:22][CH:21]([CH2:25][OH:26])[CH2:20]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3497988Morpholin-2-ylmethanolHCID 5049666Sodium triacetoxyborohydrideHCID 574483844-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzaldehyde

Product 1

HCID 44481855{4-[4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)benzyl]morpholin-2-yl}methanolYield 56%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)benzaldehyde (150 mg, 0.585 mmol) and morpholin-2-yl-methanol (82 mg, 0.702 mmol, 1.2 equiv.) in DCE (3.1 mL) was added sodium triacetoxyborohydride (211 mg, 0.995 mmol, 1.7 equiv.) in two portions over 5 min. The mixture was then allowed to stir at rt for 4 h. The mixture was then filtered and purified using preparative reverse phase HPLC to afford the desired product as a light yellow oil (116 mg, 56%). 1H NMR (600 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.01 (dd, J=7.9, 1.6, 1H), 7.42-7.35 (m, 4H), 7.20 (dd, J=7.9, 4.8, 1H), 3.95-3.87 (m, 1H), 3.75-3.61 (m, 3H), 3.60-3.48 (m, 3H), 2.70 (t, J=12.8, 2H), 2.22 (dt, J=11.5, 3.5, 1H), 2.07-1.99 (m, 1H), 1.93-1.86 (m, 1H). MS (ESI): mass calcd. for C18H19N3O3S, 357.12; m/z found, 358.1 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. custompurified

Sources & evidence

ORD record
ord-2b0d8feb517b48f89da92f26dbaab1c1
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

Loading…