Hydrochloric Acid → HCID 9948781, compound

HRID 1245644Notes

Reaction equation

HRID 1245644 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[CH3:22])(=[O:14])=[O:13])[S:9][CH:10]=1.OC1C=NC=CC=1.Cl>O1CCCC1>[Cl:21][C:17]1[C:16]([CH3:22])=[C:15]([S:12]([NH:11][C:8]2[S:9][CH:10]=[C:6]([CH:5]=[CH2:4])[N:7]=2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 11292384HCID 11292384, compound

Product 1

HCID 9948781HCID 9948781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (95% dry, 32 mg, 1.27 mmol) was added to a stirred solution of the product from Step 3 (240 mg, 0.61 mmol) and 3-hydroxypyridine (63 mg, 0.67 mmol) in tetrahydrofuran (10 mL) at 0° C. After 2 h at reflux temperature the reaction was neutralized by adding 2 M HCl and the product mixture was extracted with dichloromethane. The organic phase was dried (Na2SO4) and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel gradient eluting with 2-5% acetone in dichloromethane giving the title compound as a solid (33 mg, 17%). MS (Ionspray, [M+H]+) m/z 314; Anal. Calcd. (found) for C12H11ClN2O2S2: C 45.8 (45.0) % H 3.5 (3.9) %N 8.9(9.1) %.

Workup

  1. temperatureAfter 2 h at reflux temperature the reaction
  2. extractionthe product mixture was extracted with dichloromethane
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe crude material was purified by flash chromatography on silica gel gradient
  6. washeluting with 2-5% acetone in dichloromethane giving the title compound as a solid (33 mg, 17%)

Sources & evidence

ORD record
ord-2fb957e7f69847468ab7c81ad73de12a
Source dataset
uspto-grants-2006_10
Patent number
US07125900B2

Reaction notes

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