Trifluoroacetic acid → 6-[3-(4-(aminoiminomethyl)phenylamino)-3-oxopropyl]-3,4,5,6-tetrahydro-2H-pyran-2-one

HRID 976334Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:20])[CH2:11][CH2:12][CH:13]2[O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O.CC#[N:30].CCOCC>>[NH2:30][N:2]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:20])[CH2:11][CH2:12][CH:13]2[O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14]2)=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 190366276-[3-(4-cyanophenylamino)-3-oxopropyl]-3,4,5,6-tetrahydro-2H-pyran-2-one

HCID 21885917Acetonitrile ether

Product 1

HCID 700779716-[3-(4-(aminoiminomethyl)phenylamino)-3-oxopropyl]-3,4,5,6-tetrahydro-2H-pyran-2-one

Procedure

The title compound was prepared from the product of step B (770 mg, 2.83 mmol) in a manner similar to example 1, step G to give 430 mg (38%) of product as TFA salt after reverse phase chromatography and trituration with CH3CN/Et2O (m.p. 151°-153° C. dec.).

Sources & evidence

ORD record: ord-5e3249e1962f4e75ad970cf575400a0c
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05612355

Reaction notes

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