Sodium hydride → HCID 11523114, compound

HRID 639803Notes

Reaction equation

[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[N:11]=[N:10][C:9]([CH2:12][OH:13])=[N:8]2)[CH:2]=1.[H-].[Na+].CS([C:21]1[N:22]([CH3:32])[C:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:24][N:25]=1)(=O)=O>>[CH3:32][N:22]1[C:21]([O:13][CH2:12][C:9]2[N:10]=[N:11][N:7]([C:3]3[CH:2]=[C:1]([CH3:14])[CH:6]=[CH:5][CH:4]=3)[N:8]=2)=[N:25][N:24]=[C:23]1[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 221514774-(4-Methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl)pyridine

HCID 59424221(2-m-tolyl-2H-tetrazol-5-yl)-methanol

Product 1

HCID 11523114HCID 11523114, compoundYield 52.1%

Procedure

The title compound (23.6 mg, 52%, white solid) was prepared from (2-m-tolyl-2H-tetrazol-5-yl)-methanol (24.8 mg, 0.13 mmol), sodium hydride (8 mg, 0.2 mmol) and 4-(5-methanesulfonyl-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine (38 mg, 0.16 mmol). The product was purified by chromatography using a silica SPE tube (2.5-5% methanol in dichloromethane, desired product was second product eluting). 1H NMR (CDCl3) δ (ppm): 8.78 (m, 2H), 7.98 (s, 1H), 7.97 (d, 1H), 7.64 (d, 2H), 7.46 (t, 1H), 7.34 (d, 1H), 5.94 (s, 2H), 3.63 (s, 3H), 2.50 (s, 3H).

Workup

customThe product was purified by chromatography
wash(2.5-5% methanol in dichloromethane, desired product was second product eluting)

Sources & evidence

ORD record: ord-211d8551fcfb4d28be4035bf46a35e28
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691892B2

Reaction notes

Loading…