Sodium Methoxide → HCID 178485720, compound

HRID 482262Notes

Reaction equation

Br.[C:2]([N:5]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH:7][C:6]1=[O:12])(=[NH:4])[NH2:3].C[O-].[Na+].[CH3:16][N:17]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)[C:18](=[O:26])[C:19]([C:24]#[N:25])=[CH:20]OCC>C(O)CC.CO>[C:24]([C:19]([C:18](=[O:26])[N:17]([CH3:16])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)=[CH:20][NH:4][C:2](=[NH:3])[N:5]1[CH2:9][C:8]([CH3:10])([CH3:11])[NH:7][C:6]1=[O:12])#[N:25]

Participants

Conditions

Temperature: 45 °C

Procedure

4.74 g (20 mmol) of 1-amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromide were dissolved in 47 ml of boiling 1-propanol and, at 88°-90° C., 3.60 g (=3.67 ml, 20 mmol) of a 30% strength solution of sodium methylate in methanol were added. The resulting suspension was cooled to 45° C., stirred at 45° C. for 30 min and then cooled to 20° C., and 5.97 g (20 mmol) of 2-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amide were added at 20° C., and the mixture was stirred at room temperature for 1.8 hours. The solid which had separated out was, after dilution of the pasty mass with 50 ml of ether, filtered off with suction and washed with ether. This product (initial crystals) and the residue from the original filtrate (mother liquor) were worked up further as described in Example 1 and dried. 6.23 g (=76.3% yield) of, according to TLC, virtually pure compound IV were obtained.

Workup

temperaturecooled to 20° C.
stirringthe mixture was stirred at room temperature for 1.8 hours
customThe solid which had separated out
filtrationafter dilution of the pasty mass with 50 ml of ether, filtered off with suction
washwashed with ether
customdried

Sources & evidence

ORD record: ord-15e562511bde4f8c9bdbb3436fd7b4c2
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795899

Reaction notes

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