HCID 19066320, compound → HCID 178501432, compound

HRID 481442Notes

Reaction equation

HRID 481442 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N:22]([CH3:46])[CH:23]2[C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][C:26]=3[CH2:25][CH2:24]2)[N:33]=[C:32]([CH3:36])[N:31]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:30]4=[O:45])[CH:19]=[CH:18][C:3]=1[C:4](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:5].[NH2:47][C@@H:48]([CH2:53][CH2:54][C:55]1[NH:59][N:58]=[N:57][N:56]=1)[C:49]([O:51][CH3:52])=[O:50]>>[F:1][C:2]1[CH:21]=[C:20]([N:22]([CH3:46])[CH:23]2[C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][C:26]=3[CH2:25][CH2:24]2)[N:33]=[C:32]([CH3:36])[N:31]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:41])[CH3:42])[C:30]4=[O:45])[CH:19]=[CH:18][C:3]=1[C:4]([NH:47][C@@H:48]([CH2:53][CH2:54][C:55]1[NH:59][N:58]=[N:57][N:56]=1)[C:49]([O:51][CH3:52])=[O:50])=[O:5]

Participants

3

Reactant 2

HCID 19066320HCID 19066320, compoundHCID 178501500methyl (2S)-2-amino-4-(1H-1,2,3,4-tetrazol-5-yl)butanoate

Product 1

HCID 178501432HCID 178501432, compoundYield 73%

Procedure

Using analogous procedures to those described in the second and third paragraphs of Example 12, pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate was reacted with methyl (2S)-2-amino-4-(tetrazol-5-yl)butyrate to give methyl (2S)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-3-pivaloyloxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-4-(tetrazol-5-yl)butyrate in 73% yield which in turn was hydrolysed with aqueous sodium hydroxide solution to give (2S)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-4-(tetrazol-5-yl)butyric acid in 81% yield, m.p. 203°-205° C.;

Sources & evidence

ORD record
ord-b40919c73043490097f4546075ea6c6a
Source dataset
uspto-grants-1998_08
Patent number
US05789417

Reaction notes

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