6-(3-Cyano-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one → {3-[3-(3-Cyano-thiophen-2-yl)-3-oxo-propionylamino]-4'-fluoro-biphenyl-4-yl}-carbamic acid tert.-butyl ester

HRID 1635305Notes

Reaction equation

HRID 1635305 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:10][C:9]=1[NH2:21])([CH3:4])([CH3:3])[CH3:2].[C:23]([C:25]1[CH:29]=[CH:28][S:27][C:26]=1[C:30]1[O:35]C(C)(C)[O:33][C:32](=O)[CH:31]=1)#[N:24]>>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)=[CH:10][C:9]=1[NH:21][C:32](=[O:33])[CH2:31][C:30]([C:26]1[S:27][CH:28]=[CH:29][C:25]=1[C:23]#[N:24])=[O:35])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 222249166-(3-Cyano-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 59737201Tert-butyl (3-amino-4'-fluoro-[1,1'-biphenyl]-4-YL)carbamate

Product 1

HCID 86588039{3-[3-(3-Cyano-thiophen-2-yl)-3-oxo-propionylamino]-4'-fluoro-biphenyl-4-yl}-carbamic acid tert.-butyl esterYield 52.3%

Procedure

Prepared from (3-amino-4′-fluoro-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G39) (302 mg, 1.0 mmol) and 6-(3-cyano-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one (Example J3) (250 mg, 1.06 mmol) according to the general procedure K. Obtained as a light yellow solid (251 mg).

Sources & evidence

ORD record
ord-61c6b9525989497bb6d9d5f0f33a336c
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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