Glycine → [(3-Bromo-7-cyano-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acid

HRID 642453Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([O:24]C(=O)C)=[C:8]2[C:16]([Br:17])=[CH:15][N:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=O)C.[NH2:28][CH2:29][C:30]([OH:32])=[O:31].C[O-].[Na+].CO>>[Br:17][C:16]1[C:8]2[C:9](=[C:10]([C:12]#[N:13])[N:11]=[C:6]([C:4]([NH:28][CH2:29][C:30]([OH:32])=[O:31])=[O:3])[C:7]=2[OH:24])[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=1

Participants

Reactant 3

HCID 750Glycine

HCID 23694274Sodium methanolate methanol

HCID 684277694-Acetoxy-3-bromo-7-cyano-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 68426658[(3-Bromo-7-cyano-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acid

Procedure

Prepared in analogy to that of Example 1(e) from 4-acetoxy-3-bromo-7-cyano-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, glycine and NaOMe/HOMe. The title compound, ESI MS (m/z): 428 (M+H)+.

Sources & evidence

ORD record: ord-2de20770c6b743c7bc415bca19264003
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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