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

HRID 642479Notes

Reaction equation

C(O[C:4]([C:6]1[C:7]([O:25]C(=O)C)=[C:8]2[C:16]([CH3:17])=[CH:15][N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])C.[NH2:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+].CO>>[CH2:18]([N:14]1[C:9]2=[C:10]([C:12]#[N:13])[N:11]=[C:6]([C:4]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:5])[C:7]([OH:25])=[C:8]2[C:16]([CH3:17])=[CH:15]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 750Glycine

HCID 23694274Sodium methanolate methanol

HCID 684273064-Acetoxy-1-benzyl-7-cyano-3-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 68427936[(1-Benzyl-7-cyano-4-hydroxy-3-methyl-1H-pyrrolo[2,3-c]pyridine-5-carbonyl)-amino]-acetic acid

Procedure

Prepared in analogy to that of Example 1(e) from 4-acetoxy-1-benzyl-7-cyano-3-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester, glycine and NaOMe/HOMe. The title compound, ESI MS (m/z): 365 (M+H)+.

Sources & evidence

ORD record: ord-45443af80d9549848dcb2174e68d5484
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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