Pyridine → HCID 24960138, compound

HRID 1430630Notes

Reaction equation

HRID 1430630 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9](=[O:21])[C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[N:15]=2)([CH3:12])[CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Cl:20][C:16]1[N:15]=[C:14]([O:13][C:10]([CH3:12])([CH3:11])[C:9]([NH:8][C:3]2[C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:21])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 24960136HCID 24960136, compound

Product 1

HCID 24960138HCID 24960138, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-Amino-pyridin-2-yl)-2-(6-chloro-pyridin-2-yloxy)-2-methyl-propionamide (0.15 g, 4.9 mmol) and pyridine (0.042 g, 5.3 mmol) in DCM (5 ml) at 0° C. was added Methane sulfonyl chloride (0.06 g, 0.04 ml, 5.3 mmol) drop wise over a period of 5 min. The reaction mixture was stirred for 1 h. The reaction mixture was quenched with water (2 ml) extracted in DCM (20 ml), washed with brine (5 ml), dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. The crude material thus obtained was purified by flash column affording 2-(6-Chloro-pyridin-2-yloxy)-N-(3-methanesulfonylamino-pyridin-2-yl)-2-methyl-propionamide (0.08 g, 5%). 1H NMR (400 MHz, CDCl3): δ 1.790 (s, 6H), 2.87 (s, 3H), 6.67 (t, 1H, J=8 Hz), 6.78 (d, 11-1, J=8 Hz), 6.91 (d, 1H, J=8 Hz), 7.18 (d, 1H, J=8 Hz), 7.57 (t, 1H, J=8 Hz), 8.69 (d, 1H, J=8 Hz), 9.11 (brs, 1H). MS (EI) m/z: 385 (M+1).

Workup

  1. customThe reaction mixture was quenched with water (2 ml)
  2. extractionextracted in DCM (20 ml)
  3. washwashed with brine (5 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude product
  7. customThe crude material thus obtained
  8. customwas purified by flash column

Sources & evidence

ORD record
ord-f26f91c6c3a3411d8eb41cac95622529
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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