Water → 2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-8-methoxy-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulene

HRID 1629134Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[C:10]1[N:11]([CH2:24][CH2:25][OH:26])[CH:12]=[C:13]([C:15]2[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]([CH3:20])[N:19]=2)[N:14]=1.[H-].[Na+].O>CN(C=O)C>[CH:21]([N:16]1[C:15]([C:13]2[N:14]=[C:10]3[N:11]([CH2:24][CH2:25][O:26][C:2]4[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=43)[CH:12]=2)=[N:19][C:18]([CH3:20])=[N:17]1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-[2-(4-chloro-6-methoxy-pyridin-3-yl)-4-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-imidazol-1-yl]-ethanol (2.25 g, 5.97 mmol) in DMF (30 mL) was cooled to 0° C. and treated with sodium hydride (239 mg, 5.97 mmol), the reaction mixture stirred at 0° C. for 30 min then allowed to warm to RT and stirred for 2 h. The reaction mixture was re-cooled to 0° C. and treated with water (400 mL), the precipitated product filtered off and washed with water then dried in vacuo to give the title compound as a white solid (1.02 g, 50%). LCMS RT=2.68 min, [M+H]+=341. 1H NMR 400 MHz (DMSO-d) δ: 9.15 (1 H, s), 7.87 (1 H, s), 6.42 (1 H, s), 5.84 (1 H, m), 4.57-4.56 (4 H, m), 3.89 (3 H, s), 2.25 (3 H, s), 1.46 (6 H, d, J=6.60 Hz).

Workup

temperatureto warm to RT
stirringstirred for 2 h
temperatureThe reaction mixture was re-cooled to 0° C.
filtrationthe precipitated product filtered off
washwashed with water
customthen dried in vacuo

Sources & evidence

ORD record: ord-68eaddb5d88849e0b056a7c9786cdc32
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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