Hydrochloric Acid → HCID 178480645, compound

HRID 854392Notes

Reaction equation

HRID 854392 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:25]([O-])=O.[Na+].C([O-])(O)=O.[Na+].[ClH:34]>O>[ClH:34].[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([C:13]2[N:12]=[C:11]3[C:10]([S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:9])=[O:8])=[N:25][NH:17][C:16]3=[CH:15][CH:14]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 589340632-[(Phenylsulfonyl)methyl]-6-(4-methylpiperazin-1-yl)-pyridin-3-ylamine

Product 1

HCID 178480645HCID 178480645, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 2-[(phenylsulfonyl)methyl]-6-(4-methylpiperazin-1-yl)-pyridin-3-ylamine (1.20 g, 3.50 mmol) in 1.0 M aqueous hydrochloric acid (20 mL) is cooled in an ice bath, treated dropwise with NaNO2 (358 mg, 5.2 mmol) in water, stirred for 1 h, treated with aqueous saturated NaHCO3 and filtered. The brown solid filtercake is washed with water, dried in vacuo, triturated with acetone and filtered. The filtercake is washed with ether and air-dried to afford the free amine of the title compound as a tan solid, 0.50 g. This solid is dissolved in a mixture of ethanol and 4.0 M HCl in dioxane and concentrated in vacuo. The resultant residue is triturated with ether to afford the title compound as an off-white solid, mp>250° C., identified by mass spectral and NMR analyses.

Workup

  1. filtrationfiltered
  2. washThe brown solid filtercake is washed with water
  3. customdried in vacuo
  4. customtriturated with acetone
  5. filtrationfiltered
  6. washThe filtercake is washed with ether
  7. customair-dried

Sources & evidence

ORD record
ord-e34926c18ab44439a4263b80bd4bd426
Source dataset
uspto-grants-2007_08
Patent number
US07259165B2

Reaction notes

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