Cesium carbonate → HCID 66893591, compound

HRID 2381535Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:31])[CH:9]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([O:21]N3C4C=CC=CC=4N=N3)[CH:16]=[N:15]2)[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:38]1[C:46]2[CH:45]=[CH:44][CH:43]=[C:42](O)[C:41]=2[CH:40]=[CH:39]1>C(#N)C.[Cl-].[NH4+]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:31])[CH:9]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([O:21][C:42]3[CH:43]=[CH:44][CH:45]=[C:46]4[C:41]=3[CH:40]=[CH:39][NH:38]4)[CH:16]=[N:15]2)[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-[4-(benzotriazol-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide (170.3 mg, 0.403 mmol) in acetonitrile (8.4 mL, 0.048M) was treated with cesium carbonate (0.26 g, 0.798 mmol) and 1H-indol-4-ol (64.3 mg, 0.483 mmol). The resulting reaction mixture was heated at 80° C. overnight. At this time, the reaction mixture was allowed to cool to 25° C. and was treated with a saturated aqueous ammonium chloride solution (5 drops). The reaction was then concentrated in vacuo onto silica gel. Silica gel column chromatography (AnaLogix 24 g, 1-10% methanol/methylene chloride) afforded impure 2-[4-(1H-indol-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide (110.9 mg, 65%) as a brown solid.

Workup

customThe resulting reaction mixture
temperatureto cool to 25° C.
concentrationThe reaction was then concentrated in vacuo onto silica gel

Sources & evidence

ORD record: ord-d307b987e30b4607bf3414eec1f026d0
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

Loading…