Cyclohexylamine → 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid cyclohexylarnide
Reaction equation
Cl[C:2]1[C:3]2[CH:13]=[CH:12]SC=2NC(=O)[C:7]=1[C:8]#[N:9].C(O[C:17]([C:19]1[C:24](=[O:25])[NH:23][C:22]2[S:26][CH:27]=[CH:28][C:21]=2[C:20]=1[OH:29])=[O:18])C.C1(N)CCCCC1>>[CH:8]1([NH:9][C:17]([C:19]2[C:24](=[O:25])[NH:23][C:22]3[S:26][CH:27]=[CH:28][C:21]=3[C:20]=2[OH:29])=[O:18])[CH2:7][CH2:2][CH2:3][CH2:13][CH2:12]1Participants
Procedure
To yield compounds of structure (III) with R2 as carbonitrile, and R1 and R3 as defined above, 4-chloro-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile, depicted by formula (50), was used as a key intermediate. To prepare this intermediate, 4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester, depicted by formula (40), was reacted with cyclohexylamine to yield intermediate 4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid cyclohexylamide, depicted by formula (48). This intermediate was converted to 4,6-dichloro-thieno[2,3-b]pyrdine-5-carbonitrile, depicted by formula (49), by reacting with phosphorous oxychloride, which was then converted into 4-chloro-6-oxo-6,7-dihydro-2-thieno[2,3-b]pyridine-5-carbonitrile, depicted by formula (50), as shown in Scheme 25.
Sources & evidence
- ORD record
- ord-15195c2c3ccd464ab2edb8894b503f3e
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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