Cyclohexylamine → HCID 59702050, compound
Reaction equation
Cl[C:2]1[C:10]2[C:6](=[CH:7]SC=2)NC(=O)[C:3]=1[C:12]#[N:13].C(O[C:17]([C:19]1[C:20](=[O:29])[NH:21][C:22]2[C:26]([C:27]=1[OH:28])=[CH:25][S:24][CH:23]=2)=[O:18])C.C1(N)CCCCC1>>[CH:12]1([NH:13][C:17]([C:19]2[C:20](=[O:29])[NH:21][C:22]3[C:26]([C:27]=2[OH:28])=[CH:25][S:24][CH:23]=3)=[O:18])[CH2:3][CH2:2][CH2:10][CH2:6][CH2:7]1Participants
Procedure
To prepare compounds of structure (II) with R2 as carbonitrile, and R1 and R3 as defined above, 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carbonitrile, depicted by formula (33), was used as a key intermediate. To prepare this intermediate, 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by formula (23), was reacted with cyclohexylamine to yield intermediate 7-hydroxy-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid cyclohexylamide, depicted by formula (31). This intermediate was converted to 5,7-dichloro-2-thia-4-aza-indene-6-carbonitrile, depicted by formula (32), by reacting with phosphorous oxychloride, and was then converted into 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-6-carbonitrile, depicted by formula (33), as shown in Scheme 15.
Sources & evidence
- ORD record
- ord-ebb2cd49353346d09d83f26455786667
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365200B2
Reaction notes
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