Hydrochloric Acid → HCID 10961937, compound

HRID 1634232Notes

Reaction equation

HRID 1634232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:34])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH2:24][C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=O)[C:16]=3[CH:15]=[CH:14][C:13]=2[N:33]=1.B.CSC.Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:34])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH2:24][CH2:25][N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[C:16]=3[CH:15]=[CH:14][C:13]=2[N:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10885591HCID 10885591, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10961937HCID 10961937, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of the product of Example 7 (85 mg, 0.17 mmol) in THF (9 mL) was heated to reflux and borane-methylsulfide (0.09 mL, 0.9 mmol) added. Stirring was continued for 3.5 h at reflux and overnight at room temperature. 6M HCl was added and the solution stirred for 2 h. The solution was applied to a Varian SCX column, washed with MeOH/CH2Cl2 50:50, then the product eluted with MeOH/CH2Cl2/NH4OH 50:50:1. The product was further purified on a silica column eluting with CH2Cl2/MeOH 98:2 to give the title compound 32 mg, 39%, mp 285-290° C.; MS (ES) 486,488 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. stirringthe solution stirred for 2 h
  4. washwashed with MeOH/CH2Cl2 50:50
  5. washthe product eluted with MeOH/CH2Cl2/NH4OH 50:50:1
  6. customThe product was further purified on a silica column
  7. washeluting with CH2Cl2/MeOH 98:2

Sources & evidence

ORD record
ord-fd29e45de0794be18338437360146298
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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