Diethyl Ether → 5-Chloro-1h-indole-2-carboxylic acid [(methoxy-methyl-carbamoyl)-methyl]-amide

HRID 651102Notes

Reaction equation

Cl.CO[CH2:4][NH2:5].[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])=[CH:10]2.C[CH2:24][O:25]CC>>[CH3:24][O:25][N:5]([CH3:4])[C:20]([CH2:19][NH:18][C:16]([C:11]1[NH:12][C:13]2[C:9]([CH:10]=1)=[CH:8][C:7]([Cl:6])=[CH:15][CH:14]=2)=[O:17])=[O:22]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine

HCID 21959107Methoxymethanamine hydrochloride

Product 1

HCID 538615275-Chloro-1h-indole-2-carboxylic acid [(methoxy-methyl-carbamoyl)-methyl]-amide

Procedure

Methoxymethylamine hydrochloride (1.0 mmol) and [(5-chloro-1H-indole-2-carbonyl)-amino]-acetic acid (1.0 mmol) were coupled according to Procedure A. The resulting solid was suspended in ether, filtered and dried: Yield 158 mg, 53%; PBMS 296/298 (MH+, 100%);

Workup

filtrationfiltered
customdried

Sources & evidence

ORD record: ord-7bf8fa9d80634bd19d45a6096bd50611
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277877B1

Reaction notes

Loading…