Pyridine → HCID 136384919, compound

HRID 494605Notes

Reaction equation

HRID 494605 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, 2H) 1.15 (m, 1H) 1.26 (m, 4H) 1.47 (m, 3H) 1.57 (s, 3H) 1.72 (m, 2H) 2.14 (m, 1H) 2.31 (m, 1H) 3.08 (s, 3H) 7.53 (m, 1H) 7.61 (dd, J=11.77, 2.21 Hz, 1H) 8.15 (d, J=7.35 Hz, 1H) 10.25 (s, 1H) 13.83 (s, 1H). 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-4d9781c7418d415da2e284af3f5d1b5a
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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