Ethanol → HCID 178504904, compound

HRID 1257727Notes

Reaction equation

HRID 1257727 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:30]([O-])=O)[C:18]([NH:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([S:26]([CH3:29])(=[O:28])=[O:27])[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.C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:30])[C:18]([NH:19][C@H:20]4[CH2:21][CH2:22][C@H:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:24][CH2:25]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 178504905HCID 178504905, compound

Product 1

HCID 178504904HCID 178504904, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of trans (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(4-methanesulfonyl-cyclohexyl)-amine (585 mg, 1.20 mmol) and ethanol (4 mL, IMS grade) was treated with water (1.3 mL) followed by ammonium chloride (393 mg, 7.30 mmol) and iron powder (274 mg, 4.90 mmol). The mixture was heated to 80° C. for 45 minutes. The resulting solid was isolated and washed repeatedly with ethanol/water. The filtrate was partially concentrated under vacuum and then diluted with DCM and water. The phases were separated and the aqueous phase was extracted with DCM (×2). The combined organic extracts were washed with brine, dried with sodium sulfate and concentrated under vacuum to give 505 mg (92%) of trans 1-benzenesulfonyl-N*4*-(4-methanesulfonyl-cyclohexyl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine as a pale brown solid that was used without further purification. 1H NMR (400 MHz, DMSO) δ: 8.01 (dd, 2H), 7.70-7.64 (m, 1H), 7.55 (m, 3H), 7.47 (d, 1H), 6.76 (d, 1H), 5.13 (d, 1H), 3.72 (br s, 1H), 3.06 (m, 1H), 2.93 (s, 3H), 2.09 (m, 4H), 1.63 (m, 2H), 1.33 (m, 2H).

Workup

  1. customThe resulting solid was isolated
  2. washwashed repeatedly with ethanol/water
  3. concentrationThe filtrate was partially concentrated under vacuum
  4. additiondiluted with DCM and water
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with DCM (×2)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3133c5366a374597a4e1de85c23f90a3
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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