6-(3-Imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one → {4-(2-Fluoro-phenylethynyl)-2-[3-(3-imidazol-1-yl-phenyl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl ester

HRID 859416Notes

Reaction equation

HRID 859416 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[CH:10][C:9]=1[NH2:23])([CH3:4])([CH3:3])[CH3:2].[N:25]1([C:30]2[CH:31]=[C:32]([C:36]3[O:41]C(C)(C)[O:39][C:38](=O)[CH:37]=3)[CH:33]=[CH:34][CH:35]=2)[CH:29]=[CH:28][N:27]=[CH:26]1>>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[CH:10][C:9]=1[NH:23][C:38](=[O:39])[CH2:37][C:36]([C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH:31]=1)=[O:41])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 222248956-(3-Imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 69592833[2-Amino-4-(2-fluoro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester

Product 1

HCID 86588024{4-(2-Fluoro-phenylethynyl)-2-[3-(3-imidazol-1-yl-phenyl)-3-oxo-propionylamino]-phenyl}-carbamic acid tert.-butyl esterYield 52.2%

Procedure

Prepared from [2-amino-4-(2-fluoro-phenylethynyl)-phenyl]-carbamic acid tert.-butyl ester (Example G34) (245 mg, 0.75 mmol) and 6-(3-imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one (Example J10) (300 mg, 1.1 mmol) according to the general procedure K. Obtained as a yellow-brown foam (211 mg).

Sources & evidence

ORD record
ord-cb8b28ad7b8841d5b2c438ef5e628b78
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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