Pyridine → HCID 136384919, compound

HRID 2224925Notes

Reaction equation

HRID 2224925 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:29])[C:14]([CH2:24][CH:25]4[CH2:28][CH2:27][CH2:26]4)([CH3:23])[C:15]4[C:20]([C:21]=3[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH:25]1([CH2:24][C:14]2([CH3:23])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]([OH:22])=[C:12]([C:7]3[NH:6][C:5]4[CH:30]=[CH:31][C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:3][C:4]=4[S:9](=[O:11])(=[O:10])[N:8]=3)[C:13]2=[O:29])[CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 135430175HCID 135430175, compound

Product 1

HCID 136384919HCID 136384919, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of Example 56 (0.080 g, 0.189 mmol) and pyridine (0.122 mL, 1.512 mmol) in dichloromethane was added methanesulfonyl chloride (0.017 mL, 0.227 mmol) dropwise over 5 minutes and the resulting reaction mixture stirred for 12 hours. The solution was concentrated in. vacuo and purified by flash chromatography on SiO2 eluting with a 0-100% ethyl acetate/hexane gradient yielding the title compound (0.079 g, 84% yield) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.85 m, 2 H) 1.15 m, 1 H) 1.26 m, 4 H) 1.47 m, 3 H) 1.57 (s, 3 H) 1.72 m, 2 H) 2.14 m, 1 H) 2.31 (m, 1 H) 3.08 (s, 3H) 7.53 m, 1 H) 7.61 (dd, J=11.77, 2.21 Hz, 1 H) 8.15 (d, J=7.35 Hz, 1 H) 10.25 (s, 1 H) 13.83 (s, 1 H). MS (ESI+) m/z=516 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe solution was concentrated in
  3. customvacuo and purified by flash chromatography on SiO2 eluting with a 0-100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-38dfb3c88bd6423ba906c33ed4440147
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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