Water → HCID 86729556, compound

HRID 2280560Notes

Reaction equation

HRID 2280560 reaction equation
[Cl:1][C:2]1[C:3]([C:12](Cl)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[N:20][CH:21]=1.N1C=CC=CC=1.O>ClCCl>[Cl:1][C:2]1[C:3]([C:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24][CH3:25])=[O:23])=[N:20][CH:21]=2)=[O:13])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12457877Methyl 5-aminopyridine-2-carboxylateHCID 19995701HCID 19995701, compound

Product 1

HCID 86729556HCID 86729556, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroquinoxaline-2-carbonyl chloride (3.5 g, 15.45 mmol) in dichloromethane (32.3 mL) was added dropwise to a mixture of methyl 5-aminopyridine-2-carboxylate (2.35 g, 15.45 mmol), pyridine (3.75 mL, 46.35 mmol) and dichloromethane (48.38 mL) at 0° C. The mixture was stirred and allowed to warm up to room temperature overnight. To the reaction, water (40 mL) was added and the product precipitated. The solid was isolated by filtration, washed with water (1×40 mL) and hexanes (2×50 mL) to yield methyl 5-[(3-chloroquinoxaline-2-carbonyl)amino]pyridine-2-carboxylate (4.31 g, 81%) as a cream colored solid. 1H NMR (400 MHz, DMSO-d6) δ 11.61 (s, 1H), 9.00 (d, J=2.5 Hz, 1H), 8.46 (dd, J=8.6, 2.6 Hz, 1H), 8.36-8.26 (m, 1H), 8.24-8.12 (m, 2H), 8.12-7.95 (m, 2H), 3.89 (s, 3H) ppm. ESI-MS m/z calc. 342.05, found 343.4 (M+1)+; Retention time: 1.25 minutes (3 minutes run).

Workup

  1. additionwas added
  2. customthe product precipitated
  3. customThe solid was isolated by filtration
  4. washwashed with water (1×40 mL) and hexanes (2×50 mL)

Sources & evidence

ORD record
ord-f27bba2a0fff45fca66ed95f3fe21743
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

Loading…