HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Lithium Hydroxide → 3-(6-aminopyridin-3-yl)-N-(7-carboxy-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 1690414
Notes
Print preview

Reaction equation

HRID 1690414 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH2:14][C:15]2[C:23]3[C:18](=[C:19]([C:24]([O:26]C)=[O:25])[CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:28])[CH:16]=2)[CH3:13])=[O:11])=[CH:4][CH:3]=1.O1CCCC1.[Li+].[OH-]>CO.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([N:12]([CH2:14][C:15]2[C:23]3[C:18](=[C:19]([C:24]([OH:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:28])[CH:16]=2)[CH3:13])=[O:11])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 10407301(E)-3-(6-aminopyridin-3-yl)-N-(7-methoxycarbonyl-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Product 1

HCID 667801973-(6-aminopyridin-3-yl)-N-(7-carboxy-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamideYield 35%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

A solution of (E)-3-(6-aminopyridin-3-yl)-N-(7-methoxycarbonyl-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide (76 mg, 0.2 mmole) in methanol (4 mL), water (2 mL), and tetrahydrofuran (2 mL) was treated with LiOH (39 mg, 1.6 mmole), and the reaction was stirred at ambient temperature for 48 h. The mixture was filtered, and the filtrate was acidified to pH 4.0-4.5 with 1.0 N HCl. The precipitate was collected, washed with water and dried giving the title compound (25 mg, 35%) as a white solid: MS (ES) m/e 365.2 (M+H)+. Anal. Calcd for C20H20N4O3.0.25 H2O: C, 65.11: H, 5.60; N, 15.18. Found: C, 64.83; H, 5.52; N, 15.07.

Workup

  1. filtrationThe mixture was filtered
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8b049258c973458692b8add6492c7f1a
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153652B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes