1,4-Dioxaspiro[4.5]decan-8-ylmethanol → 2-(((4-(1,4-Dioxaspiro[4.5]dec-8-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31708Notes

Reaction equation

HRID 31708 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C@H:5](COC2C=CN=C(CO)C=2C)[CH2:4][O:3]1.[Na:19].FCC1(CF)O[CH2:26][CH:25]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][S:37]([C:39]3[NH:43][C:42]4[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=4[N:40]=3)=[O:38])[C:31]=2[CH3:48])[CH2:24]O1.O1C2(CCC(CO)CC2)OCC1>>[Na:19].[O:3]1[C:2]2([CH2:18][CH2:26][CH:25]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][S:37]([C:39]4[NH:43][C:42]5[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=5[N:40]=4)=[O:38])[C:31]=3[CH3:48])[CH2:24][CH2:1]2)[O:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanolHCID 57823107(4-(((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methylpyridin-2-yl)methanolHCID 667757672-(((4-((2,2-Bis(fluoromethyl)-1,3-dioxan-5-yl)methoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667763312-(((4-(1,4-Dioxaspiro[4.5]dec-8-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Procedure

The same procedure as in the steps (14a) to (14b) of Example 14 and the steps (7d) to (7f) of Example 7 was repeated using the 1,4-dioxaspiro[4.5]dec-8-ylmethanol obtained in the step (82a) above to obtain the title compound (115 mg, the total yield of 5 steps: 7.3%) as a white solid. Note that, in the same process as in the step (14b), after acetic anhydride was added, 2 equivalents of triethylamine relative to pyridine1-oxide derivative was added to perform the reaction.

Workup

  1. customobtained in the step (82a) above

Sources & evidence

ORD record
ord-321f1cbbd0cd4e728345bc492c738254
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

Loading…