Pyridine → HCID 136124377, compound

HRID 494641Notes

Reaction equation

HRID 494641 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:28])[C:14]([CH2:24][CH:25]4[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.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>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:29]=[CH:30][C:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])=[CH:3][C:4]=4[S:9](=[O:11])(=[O:10])[N:8]=3)[C:13]2=[O:28])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 136337592HCID 136337592, compound

Product 1

HCID 136124377HCID 136124377, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of Example 165 (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 -0.39 (m, 1H) −0.13 (m, 1H) 0.03 (m, 2H) 0.21 (m, 1H) 1.24 (m, 1H) 1.43 (s, 3H) 1.78 (m, 1H) 1.99 (m, 1H) 3.01 (s, 3H) 7.38 (m, 3H) 7.50 (m, 3H) 8.07 (d, J=7.35 Hz, 1H) 9.92 (s, 1H) 15.36 (s, 1H).). MS (ESI+) m/z=502 (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-ccf33080da1f47d4968c2626c652cdb3
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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