2,3-dihydro-1H-indene-1-carboxamide → Indanyl 1,3-oxazolidine
Reaction equation
Cl[CH2:2][CH2:3]NC(NC1C2C(=C(F)C=CC=2)CC1)=O.[CH:18]1([C:27]([NH2:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1>>[CH:18]1([CH:27]2[NH:29][CH2:3][CH2:2][O:28]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1Participants
Procedure
As depicted in Scheme 2, the reaction of an appropriately substituted indanyl amine, for example 4-fluoroindanylamine (known compound, U.S. Pat. No. 5,486,541) with 2-chloroethyl isocyanate (SM4) under basic conditions, in an appropriate solvent yielded the corresponding indanyl carboxamide intermediate (a), for example, [(2-chloroethyl)amino]-N-(4-fluoroindanyl)carboxamide. Intermediate (a) was heated under basic conditions in an appropriate solvent to yield the appropriate indanyl 1,3-oxazolidine, a compound of formula I and an intermediate (b), for example, 2-[aza(4-fluoroindanyl)methylene]-1,3-oxazolidine, described in detail in Example 2, Step B, as set forth below. Compound (b) was reacted with an isothiocyanate, for example, methyl isothiocyanate, under basic conditions yielding the corresponding amino methane-1-thione, for example, 2-[aza(4-fluoroindanyl)methylene](1,3-oxazolidin-3-yl)(methylamino)methane-1-thione, a compound of formula I, described in detail in Example 2, Step C, as set forth below.
Sources & evidence
- ORD record
- ord-cc3a70a4eee044dd8712f85061dd6a1c
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178567B2
Reaction notes
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