HCID 19063877, compound → HCID 178485720, compound

HRID 482263Notes

Reaction equation

O(C)[Na].CO.Br.[C:7]([N:10]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]1=[O:17])(=[NH:9])[NH2:8].[CH3:18][N:19]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[C:20](=[O:28])[C:21]([C:26]#[N:27])=[CH:22]OCC>CO>[C:26]([C:21]([C:20](=[O:28])[N:19]([CH3:18])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)=[CH:22][NH:9][C:7](=[NH:8])[N:10]1[CH2:14][C:13]([CH3:15])([CH3:16])[NH:12][C:11]1=[O:17])#[N:27]

Participants

Conditions

Temperature: 45 °C

Procedure

3.60 g (=3.67 ml, 20 mmol) of 30% strength NaOCH3 /CH3OH solution were added to a solution of 4.74 g (20 mmol) of 1-amidino-4,4-dimethyl-2-oxoimidazolidine hydrobromide in 47 ml of methanol at room temperature, and the mixture was stirred at 45° C. for 30 min. The solution was then cooled to 20° C. and, at 20° C., 5.97 g (20 mmol) of 2-cyano-3-ethoxyacrylic acid N-methyl-N-(3-trifluoromethylphenyl)amide were added and the mixture was stirred at 20° C. for 20 min, at room temperature for 1.5 hours and while cooling in an icebath for 30 min. The solid which had separated out was filtered off with suction, washed with ether and worked up further as described in Example 1. Likewise, the residue from the filtrate (mother liquor) was further worked up as described in Example 1 and dried. 6.35 g (=77.7% yield) of, according to TLC (CH2Cl2 /C2H5 OH=10:1), virtually pure compound IV were obtained.

Workup

temperatureThe solution was then cooled to 20° C. and, at 20° C.
stirringthe mixture was stirred at 20° C. for 20 min, at room temperature for 1.5 hours
temperaturewhile cooling in an icebath for 30 min
customThe solid which had separated out
filtrationwas filtered off with suction
washwashed with ether
customdried

Sources & evidence

ORD record: ord-5a9461b0445d45339dfc96697416e4b4
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05795899

Reaction notes

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