2-(Methylamino)ethanol → HCID 178489127, compound

HRID 895360Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH:18][N:19]=[C:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=3)=[N:23][NH:22][C:21]2=[O:35])=[CH:8][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:42][CH2:43][CH2:44][NH:45][CH3:46]>>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([C:24]2[C:20](=[N:19][NH:18][C:9]3[CH:10]=[C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:45]([CH2:44][CH2:43][OH:42])[CH3:46])=[CH:7][CH:8]=3)[C:21](=[O:35])[NH:22][N:23]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH3:32]

Participants

Reactant 3

HCID 80162-(Methylamino)ethanol

HCID 10796Cesium carbonate

HCID 178489125HCID 178489125, compound

Product 1

HCID 178489127HCID 178489127, compound

Conditions

Temperature: 50 °C

Procedure

4-{[6-(3-Bromo-propoxy)-biphenyl-3-yl]-hydrazono}-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (s) and Cs2CO3 were dissolved in 1 mL (2-hydoxy)ethylmethyl amine and the resulting solution was heated to 50° C. for one hour. The solvent was evaporated and the residue was purified by silica gel chromatography (eluent: 10% methanol/DCM) to afford 15 mg 5-(3,4-dimethoxy-phenyl)-4-[(6-{3-[(2-hydroxy-ethyl)-methyl-amino]-propoxy}-biphenyl-3-yl)-hydrazono]-2,4-dihydro-pyrazol-3-one (compound 120): HPLC (Rt): 5.525 minutes; m/e: 531.24, MS (ES+): 532.2.

Workup

customThe solvent was evaporated
customthe residue was purified by silica gel chromatography (eluent: 10% methanol/DCM)

Sources & evidence

ORD record: ord-242e965ff574405ea434d57b11cbddfc
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916798B2

Reaction notes

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