Stannous chloride dihydrate → HCID 58557615, compound

HRID 1969644Notes

Reaction equation

HRID 1969644 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:10]=3[N:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>CCO>[CH2:4]1[CH2:5][CH2:6][CH:1]([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrate3×HCID 58557990HCID 58557990, compound

Product 1

HCID 58557615HCID 58557615, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of N-cyclohexyl-5-nitro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-amine (0.111 g, 0.268 mmol, prepared using K.1 from Example #21 Step D with 4-methylbenzene-1-sulfonyl chloride, L with cyclohexylamine) in EtOH (2.5 mL) was added tin (II) chloride dihydrate (0.060 g, 0.268 mmol). The reaction mixture was heated at about 75° C. for about 75 min. Tin (II) chloride dihydrate (0.030 g, 0.134 mmol) was added and the reaction mixture was heated at about 75° C. for about 5 h. Additional tin (II) chloride dihydrate (0.060 g, 0.268 mmol) was added and the reaction mixture was heated at about 75° C. for about 14 h. The solvent was removed under reduced pressure. The residue was diluted with EtOAc (25 mL) and washed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL). The organic portion was separated. The aqueous portion was extracted with EtOAc (3×25 mL). The organic extracts were combined, dried over MgSO4, filtered, and concd under reduced pressure to give N-4-cyclohexyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.081 g, 79%) as a brown oil: LC/MS (Table 1, Method n) Rt=0.82 min; MS m/z 385 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated at about 75° C. for about 5 h
  2. temperaturethe reaction mixture was heated at about 75° C. for about 14 h
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was diluted with EtOAc (25 mL)
  5. washwashed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL)
  6. customThe organic portion was separated
  7. extractionThe aqueous portion was extracted with EtOAc (3×25 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-a6f8dc626cb0428495c55bf0d5a06351
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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