Methanol → Methyl 3-[(4-chloro-2-cyclopropylbenzyl)amino]pyridine-4-carboxylate

HRID 63058Notes

Reaction equation

HRID 63058 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14]([OH:16])=[O:15])=[C:4]([CH:19]2[CH2:21][CH2:20]2)[CH:3]=1.S(Cl)(Cl)=O.[CH3:26]O>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14]([O:16][CH3:26])=[O:15])=[C:4]([CH:19]2[CH2:21][CH2:20]2)[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 90237082HCID 90237082, compound

Product 1

HCID 90236543Methyl 3-[(4-chloro-2-cyclopropylbenzyl)amino]pyridine-4-carboxylateYield 31%

Procedure

To a solution of Example 26 (15 mg, 0.05 mmol) in MeOH (10 mL) was added thionyl chloride (1 mL) at rt. The reaction was stirred at reflux for 2 days. The solution was concentrated and purified by prep-HPLC to give 5 mg (31%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 0.70-0.73 (2H, m), 1.0-1.04 (2H, m), 2.0-2.04 (1H, m), 3.96 (2H, s), 4.74 (3H, s), 7.08 (1H, d, J=1.6 Hz), 7.14 (1H, dd, J=2.0, 8.4 Hz), 7.25 (1H, d, J=8.0 Hz), 7.91 (1H, d, J=4.0 Hz), 8.05 (1H, d, J=5.6 Hz), 8.13 (1H, s). [M+H] Calc'd for C17H17ClN2O2, 317. found, 317.

Workup

  1. temperatureat reflux for 2 days
  2. concentrationThe solution was concentrated
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-4c7ebae2fe624843b37d6735f07574d4
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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