Pyridine → HCID 68511837, compound

HRID 1404938Notes

Reaction equation

HRID 1404938 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][CH2:15]3)=[O:13])=[N:7][C:6]=2[CH:24]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].N1C=CC=CC=1>C(Cl)Cl>[N:14]1([C:12](=[O:13])[CH2:11][S:10][C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:24][C:6]=3[N:7]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59467880HCID 59467880, compound

Product 1

HCID 68511837HCID 68511837, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of compound 50 (160 g, 0.45 mmol) in dry CH2Cl2 (5 mL) was added methanesulfonyl chloride (70 μL, 0.90 mmol)) followed by dropwise addition of pyridine (100 μL, 1.40 mmol). The reaction was stirred overnight under N2. The reaction mixture was diluted with CH2Cl2 (40 mL), washed with 1N HCl (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL). Dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the product was purified by column chromatography (EtOAc/hexanes 1:1) to afford 54 as a pale yellow solid (117 mg, 60%); MS m/z: 434 (M+H)+. Anal. Calcd. For, C19H19N3O3S2: C, 52.63; H, 4.42; N, 9.69; S, 22.19. Found: C, 52.69; H, 4.49; N, 9.54; S, 22.11.

Workup

  1. washwashed with 1N HCl (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL)
  2. dry with materialDried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customthe product was purified by column chromatography (EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-df825a03d2754247ad26d89b135b6ddb
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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