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

HRID 18342Notes

Reaction equation

HRID 18342 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

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 887MethanolSolventHCID 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 C20H20N4O3.0.25H2O: 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-6e9f7458e6ef462b8efad7535db0a991
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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