Isopropanol → HCID 16113437, compound

HRID 2240970Notes

Reaction equation

[F:1][CH:2]([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19]C=2)C=O)=O)=[CH:6][CH:5]=1.Cl.[CH3:24][NH:25][C:26]([NH2:28])=[NH:27].[C:29](=[O:32])([O-])[O-].[Na+].[Na+].[CH:35]([OH:38])(C)C>>[NH2:27][C:26]1[N:25]([CH3:24])[C:29](=[O:32])[C:10]([C:11]2[CH:13]=[C:14]([CH:15]=[CH:18][CH:19]=2)[CH:35]=[O:38])([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:22])=[CH:9][CH:8]=2)[N:28]=1

Participants

Reactant 4

HCID 3776Isopropanol

HCID 10340Sodium Carbonate

HCID 597903033-[2-(4-Difluoromethoxyphenyl)-2-oxo-acetyl]benzaldehyde

HCID 178485118HCID 178485118, compound

Product 1

HCID 16113437HCID 16113437, compoundYield 93%

Conditions

Temperature: 86 °C

Procedure

In a 50 ml round bottom flask was dissolved 3-[2-(4-Difluoromethoxy-phenyl)-2-oxo-acetyl]-benzaldehyde (96 mg, 0.320 mmol) in isopropanol (20 mL). Methylguanidine hydrochloride (0.071 g, 0.700 mmol) was added followed by sodium carbonate (0.070 g, 105.99 g/mol, 0.71 mmol). The mixture was heated (oil bath 86° C.) for 15½ hours, cooled to ambient temperature, and concentrated onto silica gel. Purification by column chromatography [step gradient (70% EtOAc in hexanes, EtOAc, then 20% MeOH/EtOAc-100%)] afforded 0.105 gm of a white solid (93%) 1H NMR (400 MHz, DMSO-d6) δ ppm 2.96 (s, 3H) 6.76 (br. s., 2H) 7.09 (d, J=8.8 Hz, 2H) 7.15 (t, J=74.12 Hz, 1H) 7.44 (d, J=8.8 Hz, 2H) 7.52 (t, J=7.7 Hz, 1H) 7.75 (dq, J=11.0, 3.1 Hz, 2H) 7.96 (t, J=1.5 Hz, 1H) 9.93 (s, 1H).

Workup

temperaturecooled to ambient temperature
concentrationconcentrated onto silica gel
customPurification by column chromatography [step gradient (70% EtOAc in hexanes, EtOAc

Sources & evidence

ORD record: ord-71d684d92d704148b7498b961c60d91a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723368B2

Reaction notes

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