Pyridine → HCID 49839675, compound

HRID 449933Notes

Reaction equation

HRID 449933 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.N1C=CC=CC=1.Cl[C:26](OC1C=CC=CC=1)=[O:27].[CH3:35][O:36][CH2:37][CH2:38][CH2:39][NH2:40]>C1COCC1>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:26]([NH:40][CH2:39][CH2:38][CH2:37][O:36][CH3:35])=[O:27])[CH:7]=1)=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 16723-MethoxypropylamineHCID 15891Phenyl chloroformateHCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 49839675HCID 49839675, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-amino-pyridin-4-yl)-2,6-dichloro-benzamide (281 mg, 1.0 mmol) in anhydrous THF (5 mL) were added pyridine (97 μL, 1.2 mmol) and phenyl chloroformate (138 μL, 1.1 mmol). The reaction mixture was stirred at room temperature for 1 hr and then 3-methoxy propylamine (123 μL, 1.2 mmol) was added. The reaction mixture was stirred for 1 hr then partitioned between EtOAc (10 mL) and water (10 mL). The organic layer was washed with 1 N HCl, water and brine, dried over sodium sulfate, and concentraged under reduced pressure. The residue was purified by silica gel column chromatography (EtOAC/cyclohexane: gradient 0% to 100%) to give the desired compound (105 mg, yield: 26%). NMR (400 MHz, DMSO-d6): δ 11.09 (br s, 1H), 9.18 (br s, 1H), 8.20 (br s, 1H), 8.09 (d, J=5.7 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.57-7.58 (m, 2H), 7.51 (dd, J=9.2, 6.8 Hz, 1H), 7.24 (dd, J=5.7, 1.9 Hz, 1H), 3.37 (t, J=6.2 Hz, 2H), 3.24 (s, 3H), 3.21-3.19 (m, 2H), 1.69 (m, 2H). LCMS (ESI) m/z: 397, 399 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred for 1 hr
  2. customthen partitioned between EtOAc (10 mL) and water (10 mL)
  3. washThe organic layer was washed with 1 N HCl, water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe residue was purified by silica gel column chromatography (EtOAC/cyclohexane: gradient 0% to 100%)

Sources & evidence

ORD record
ord-ba188d84961b4d91b928b72d130184a6
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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