Pyridine → HCID 59212381, compound

HRID 2243863Notes

Reaction equation

HRID 2243863 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=O)[C:3]1=[O:23].[F:24][C:25]1[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=1.N1C=CC=CC=1>O=S(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([NH:31][C:28]2[CH:27]=[CH:26][C:25]([F:24])=[CH:30][N:29]=2)=[O:18])[C:3]1=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27377012-Amino-5-fluoropyridineHCID 59212472HCID 59212472, compound

Product 1

HCID 59212381HCID 59212381, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylbenzoic acid 29 (154 mg, 0.5 mmol) in SOCl2 (1 mL) is heated at reflux for 2 h. Excess SOCl2 is removed in vacuo and the resultant solid is added to a solution of 5-fluoropyridin-2-amine (112 mg, 1 mmol) and pyridine (0.4 mL, 5 mmol) at rt. The resulting mixture is stirred for 30 min and evaporated. The residue is purified by preparative LC/MS to give the desired product M32 as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (s, 1H), 8.28 (m, 1H), 8.04 (s, 1H), 7.95 (dd, J=8, 2 Hz, 1H), 7.86 (d, J=1.9 Hz, 1H), 7.65 (dt, J=9.1, 2.9 Hz, 1H), 7.57 (s, 1H), 7.48 (d, J=8 Hz, 1H), 3.8 (s, 3H), 2.73 (s, 3H), 2.32 (s, 3H); LC/MS (M+1, m/z): 403.1.

Workup

  1. temperatureat reflux for 2 h
  2. customExcess SOCl2 is removed in vacuo
  3. customevaporated
  4. customThe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-6e39dd2e073042dbaeae7102e470056e
Source dataset
uspto-grants-2010_03
Patent number
US07678792B2

Reaction notes

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