Methanamine, N-methoxy-, hydrochloride (1:1) → 5-Chloro-1H-indole-2-carboxylic acid [(2RS)-hydroxy-2-(methoxy-methyl-carbamoyl)-ethyl]-amide

HRID 379017Notes

Reaction equation

HRID 379017 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[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][CH:20]([OH:24])[C:21]([OH:23])=O)=[O:17])=[CH:10]2>>[OH:24][CH:20]([C:21](=[O:23])[N:3]([O:4][CH3:5])[CH3:2])[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]

Participants

3

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 225938353-[(5-chloro-1H-indole-2-carbonyl)-amino]-(2RS)-hydroxy-propionic acid

Product 1

HCID 865845105-Chloro-1H-indole-2-carboxylic acid [(2RS)-hydroxy-2-(methoxy-methyl-carbamoyl)-ethyl]-amideYield 69%

Procedure

N,O-Dimethylhydroxylamine hydrochloride (1.0 mmol) and 3-[(5-chloro-1H-indole-2-carbonyl)-amino]-(2RS)-hydroxy-propionic acid (0.95 mmol) were coupled according to Procedure A (0-25° C., washed with acid, then base) and the crude product triturated with ether giving a colorless solid: Yield 69%; HPLC (60/40) 3.18 minutes (96%); mp 192-192.5° C.; PBMS 326/328 (MH+, 100%);

Workup

  1. custom0-25° C.
  2. washwashed with acid
  3. custombase) and the crude product triturated with ether giving a colorless solid
  4. customHPLC (60/40) 3.18 minutes (96%)

Sources & evidence

ORD record
ord-a8d8b825f2814fa58565001388837dcb
Source dataset
uspto-grants-2001_10
Patent number
US06297269B1

Reaction notes

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