Triethylamine → Carbonic acid 2-{3-[(4-cyanophenylimino)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]-2-fluoro-5-methoxyphenoxy}ethyl ester methyl ester

HRID 2089683Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([C:16](=[N:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[C:17](=[N:20][C:21]([O:23]C)=O)SC)[C:9]=1[F:34].[N:36]1[CH:41]=[CH:40][CH:39]=[N:38][C:37]=1[NH:42][NH2:43].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:35])[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([C:16](=[N:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=2)[C:17]2[NH:20][C:21](=[O:23])[N:42]([C:37]3[N:38]=[CH:39][CH:40]=[CH:41][N:36]=3)[N:43]=2)[C:9]=1[F:34]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the crude product containing carbonic acid {3-[1-(4-cyanophenylimino)-2-methoxycarbonylimino-2-methylsulfanylethyl]-2-fluoro-5-methoxyphenoxy}ethyl ester methyl ester (37 g, 73.4 mmol), toluene (740 mL), pyrimidin-2-yl-hydrazine (8.08 g, 73.4 mmol), and triethylamine (12.3 mL, 88.2 mmol) was heated at 50° C. for 10 minutes under stirring, gradually heated to 110° C., and heated at 110° C. for 4 hours under stirring. The mixture was gradually cooled to room temperature, and then the precipitate was filtered and dried to obtain the captioned compound (23.89 g) as a pale yellow powder.

Workup

temperaturegradually heated to 110° C.
temperatureheated at 110° C. for 4 hours
stirringunder stirring
temperatureThe mixture was gradually cooled to room temperature
filtrationthe precipitate was filtered
customdried

Sources & evidence

ORD record: ord-fcc0a514e38a4dfd8810a1567b7079c0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436009B2

Reaction notes

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