Phenacyl bromide → [3-Amino-4-ethyl-5-(4-phenoxy-phenylamino)-thiophen-2-yl]-phenyl-methanone

HRID 1260335

Reaction equation

C(#N)CC.[N:5]([CH:8]1C[CH2:11][CH2:10][CH2:9]1)=C=S.BrCC(C1ON=C(C2C=CC=CC=2)C=1)=O.C(#N)CCC.[O:33]([C:40]1[CH:45]=[CH:44][C:43]([N:46]=[C:47]=[S:48])=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Br[CH2:50][C:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:52]>>[NH2:5][C:8]1[C:9]([CH2:10][CH3:11])=[C:47]([NH:46][C:43]2[CH:44]=[CH:45][C:40]([O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:41][CH:42]=2)[S:48][C:50]=1[C:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:52]

Participants

Reactant 6

HCID 6259Phenacyl bromide

HCID 7854Propionitrile

HCID 8008Butyronitrile

HCID 141792Cyclopentyl isothiocyanate

HCID 1456941-Isothiocyanato-4-phenoxybenzene

HCID 27355325-(Bromoacetyl)-3-phenylisoxazole

Product 1

HCID 57837075[3-Amino-4-ethyl-5-(4-phenoxy-phenylamino)-thiophen-2-yl]-phenyl-methanone

Procedure

[3-Amino-4-ethyl-5-(4-phenoxy-phenylamino)-thiophen-2-yl]-phenyl-methanone was prepared as described in Example 43 substituting Propanenitrile, Isothiocyanato-cyclopentane and 2-Bromo-1-(3-phenyl-isoxazol-5-yl)-ethanone with butanenitrile, 4-phenoxyphenylisothiocyanate and 2-Bromo-1-phenyl-ethanone respectively to provide compound 1-243. MS (ESI) [M+H+]+=415.0

Sources & evidence

ORD record: ord-f6f596802c31474eb7b7c8c48449808e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470821B2

Linked notes

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