Ammonium Hydroxide → HCID 68857527, compound

HRID 1986304Notes

Reaction equation

HRID 1986304 reaction equation
[Cl:1][C:2]1[C:3]([C:19]2[S:23][C:22]3[CH:24]=[C:25](S[Si](C(C)C)(C(C)C)C(C)C)[CH:26]=[CH:27][C:21]=3[CH:20]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:6][CH:7]=1.[N+]([O-])([O-])=O.[K+].[S:44](Cl)(Cl)(=[O:46])=[O:45].[OH-].[NH4+:50]>C(#N)C.O>[Cl:1][C:2]1[C:3]([C:19]2[S:23][C:22]3[CH:24]=[C:25]([S:44]([NH2:50])(=[O:46])=[O:45])[CH:26]=[CH:27][C:21]=3[CH:20]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 24648Sulfuryl chlorideHCID 68856205HCID 68856205, compound

Product 1

HCID 68857527HCID 68857527, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of [5-chloro-4-(6-triisopropylsilanylsulfanylbenzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine (463 mg, 0.784 mmol) in acetonitrile (4 mL) is added potassium nitrate (198 mg, 1.96 mmol) followed by the dropwise addition of sulfuryl chloride (0.157 mL, 1.96 mmol). The mixture is stirred at room temperature for 1.5 hours. After filtration, the solid is suspended in acetone (5 mL) and a solution of ammonium hydroxide (0.926 mL, 15.7 mmol) is added dropwise at 0° C. After stirring at 0° C. for 1 hour, water (40 mL) is added and the mixture is extracted with EtOAc (3×50 mL). The organic layers are concentrated and the crude product is purified on silica gel, eluting with dichloromethane in MeOH 10:0 to 6:4. The solid obtained is washed with MeOH to give the title compound as a yellow solid (26 mg, 7% yield). ES+(m/z) 481 (35Cl) and 483 (37Cl) [M+H].

Workup

  1. filtrationAfter filtration
  2. stirringAfter stirring at 0° C. for 1 hour
  3. extractionthe mixture is extracted with EtOAc (3×50 mL)
  4. concentrationThe organic layers are concentrated
  5. customthe crude product is purified on silica gel
  6. washeluting with dichloromethane in MeOH 10:0 to 6:4
  7. customThe solid obtained
  8. washis washed with MeOH

Sources & evidence

ORD record
ord-b4a7712cc7824a108a75430fbd8ec28b
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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