Sodium Hydroxide → HCID 21878493, compound

HRID 723959Notes

Reaction equation

HRID 723959 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][NH:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:13]=2[N:14]=1.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][NH:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 21878481HCID 21878481, compound

Product 1

HCID 21878493HCID 21878493, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5 mL of ethanol was added [2-(1-Methyl-pyrrolidin-2-yl)-ethyl]-(5-nitro-benzothiazol-2-yl)-amine (Example 25(a), 177.4 mg, 0.577 mmol) and tin(II) chloride dihyrdate (948 mg, 5 eq.). The resulting solution was heated at reflux for 4 hours. After cooling to room temperature, the mixture was poured onto 100 mL of a 1.5 M NaOH solution. The mixture was extracted using ethyl acetate (3×100 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel using 10% 2M ammonia/methanol in dichloromethane (98.4 mg, 62%). 1H NMR (CDCl3) δ: 7.32 (d, 1H, J=8.5 Hz), 6.91 (d, 1H, J=1.9 Hz), 6.49 (dd, 1H, J=1.9, 8.5 Hz), 3.67 (br s, NH2), 3.51 (m, 2H), 3.13–3.09 (m, 1H), 2.36 (s, 4H), 2.19 (m, 1H), 1.93–1.68 (m, 6H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 4 hours
  3. extractionThe mixture was extracted
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using 10% 2M ammonia/methanol in dichloromethane (98.4 mg, 62%)

Sources & evidence

ORD record
ord-022ec9d9f805478c92a236bb46e16340
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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