Reaction equation
CC1NC(=O)C2C(=CC3CCC(N([C:20]4[CH:21]=[CH:22][C:23]([C:26]([OH:28])=[O:27])=[N:24][CH:25]=4)CC#C)C=3C=2)N=1.FC(F)(F)C(O[C:34]1[C:39]([F:40])=[C:38]([F:41])[C:37]([F:42])=[C:36]([F:43])[C:35]=1[F:44])=O>>[N:24]1[CH:25]=[CH:20][CH:21]=[CH:22][C:23]=1[C:26]([O:28][C:34]1[C:35]([F:44])=[C:36]([F:43])[C:37]([F:42])=[C:38]([F:41])[C:39]=1[F:40])=[O:27]Participants
Procedure
Using analogous procedures to those described in Example 12, 5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridine-2-carboxylic acid was reacted with pentafluorophenyl trifluoroacetate to give the pentafluorophenyl pyridine-2-carboxylate which was in turn reacted with tri-tert-butyl L-γ-glutamyl-D-glutamate (European Patent Application No. 0509643, Example 1 thereof) to give tri-tert-butyl N-{5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridyl-2-carbonyl -L-γ-glutamyl-D-glutamate in 98% yield which was in turn hydrolysed with aqueous sodium hydroxide solution to give N-{5-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]pyridyl-2-carbonyl}-L-γ-glutamyl-D-glutamic acid in 68% yield, m.p. 196° C.;
Sources & evidence
- ORD record
- ord-2b9bed8a190c48129ee532b0c9478b0a
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789417
Linked notes
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