Phenol → 2-Furan-2-yl-6-(3-phenoxy-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine
Reaction equation
Br[C:2]1[N:3]=[C:4]([NH2:16])[C:5]2[N:6]([N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:7]=1.[CH2:17]([OH:20])[C:18]#[CH:19].[C:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[N:10]=[C:5]2[C:4]([NH2:16])=[N:3][C:2]([C:19]#[C:18][CH2:17][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:7][N:6]2[N:8]=1Participants
6
Procedure
Alternatively, a compound of formula (I) can react with an alkynyl (e.g., a compound of the formula L′-X1a where L′ is a precursor of L and X1a has been defined above) to form an intermediate, which can further react with a compound of the formula R1—X3—Y—X2-L″ to form a compound of formula (I). As an example, 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine can react with prop-2-yn-1-ol to form 3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-prop-2-1-ol, which can then react with phenol in the presence of triphenyl phosphine and diisopropyl azodicarboxylate to form 2-furan-2-yl-6-(3-phenoxy-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine, a compound of formula (I). See, e.g., Example 22 below.
Workup
- customto form 3-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-prop-2-1-ol, which
Sources & evidence
- ORD record
- ord-cd222f27e4ed46a599702c3459c014d7
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674791B2
Reaction notes
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