Ammonium Chloride → HCID 178504875, compound

HRID 1257730Notes

Reaction equation

HRID 1257730 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:32]([O-])=O)[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+]>C(O)C.O.C(Cl)Cl.[Fe]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:32])[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 178504877HCID 178504877, compound

Product 1

HCID 178504875HCID 178504875, compoundYield 106.4%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

Trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-[4-(2-methanesulfonyl-ethyl)-cyclohexyl]-amine (1.04 g, 2.05 mmol) was suspended in a mixture of ethanol (10 mL, IMS grade) and water (3.3 mL). Ammonium chloride (658 mg, 12.3 mmol) was added, followed by iron (dust, 460 mg, 8.20 mmol), and the mixture was heated at 100° C. for 2 h. The mixture was cooled to room temperature, then diluted with a 4:1 mixture of DCM: 2 M ammonia in methanol and filtered through Celite®. The filter cake was washed with further 4:1 DCM: 2 M ammonia in methanol and the combined filtrate was concentrated under vacuum. The residue was suspended in water and extracted with DCM (×3). The combined organic extracts were washed with brine then dried (Na2SO4) and concentrated to give 1.04 g (quant) of crude trans 1-benzenesulfonyl-N*4*-[4-(2-methanesulfonyl-ethyl)-cyclohexyl]-1H-pyrrolo[2,3-b]pyridine-4,5-diamine, which was used directly without further purification. LCMS (Method Q, ESI): RT=2.62 min, m+H=477.1.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtration2 M ammonia in methanol and filtered through Celite®
  3. washThe filter cake was washed with further 4:1 DCM
  4. concentration2 M ammonia in methanol and the combined filtrate was concentrated under vacuum
  5. extractionextracted with DCM (×3)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialthen dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-09e550428a4446259ee953917bd15427
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…