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 → HCID 178456765, compound

HRID 481439Notes

Reaction equation

HRID 481439 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][CH:13]([N:16]([C:20]4[CH:21]=[CH:22][C:23]([C:26](O)=[O:27])=[N:24][CH:25]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1.[NH2:29][C@@H:30]([CH2:35][CH2:36][C:37]1[NH:41][N:40]=[N:39][N:38]=1)[C:31]([O:33]C)=[O:32]>>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]3[CH2:15][CH2:14][CH:13]([N:16]([C:20]4[CH:21]=[CH:22][C:23]([C:26]([NH:29][C@@H:30]([CH2:35][CH2:36][C:37]5[NH:41][N:40]=[N:39][N:38]=5)[C:31]([OH:33])=[O:32])=[O:27])=[N:24][CH:25]=4)[CH2:17][C:18]#[CH:19])[C:7]=3[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 1358483075-[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 acidHCID 178501500methyl (2S)-2-amino-4-(1H-1,2,3,4-tetrazol-5-yl)butanoate

Product 1

HCID 178456765HCID 178456765, compoundYield 33%

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 methyl (2S)-2-amino-4-(tetrazol-5-yl)butyrate to give (2S)-2-{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-carboxamido}-4-(tetrazol-5-yl)butyric acid in 33% yield, m.p. 189°-191° C.;

Sources & evidence

ORD record
ord-ae687ba1cc2c4abab105f1129ceec57f
Source dataset
uspto-grants-1998_08
Patent number
US05789417

Reaction notes

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