1,5-Diazabicyclo(4.3.0)non-5-ene → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1042341

Reaction equation

[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1CN2C(=NCCC2)C1.[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH:31](Br)C)[N:30]=1>CC#N>[Br:25][C:26]1[S:27][CH:28]=[C:29]([CH2:31][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.7 g, 3.44 mmol, 1.0 eq.) in 25 ml of MeCN, was added dropwise DBN (0.42 g, 3.44 mmol, 1.0 eq.). The reaction was stirred for 5 mins before addition of 2-bromo-4-(1-bromoethyl)-1,3-thiazole (0.86 g, 3.2 mmol, 0.93 eq.) portionwise. The mixture was stirred for further 5 mins before removal of the cooling bath and continued at ambient temperature. LCMS after 2 h would indicate reaction complete. MeCN was evaporated and the residue was purified by chromatography on silica gel to yield N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (6.9 g, 79% yield, 9:1 mixture of stereoisomers).

Workup

customcontinued at ambient temperature
waitLCMS after 2 h would indicate
customreaction complete
customMeCN was evaporated
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-263d67cf9e924700af90064f0277fc34
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557849B2

Linked notes

Loading…