Water → HCID 67344043, compound

HRID 1257588Notes

Reaction equation

HRID 1257588 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:41]([O-])=O)[C:18]([NH:19][CH:20]4[CH2:28][CH:27]5[CH:23]([CH2:24][C:25](=[O:40])[N:26]5[CH2:29][C:30]5[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=5[O:38][CH3:39])[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+].O>C(O)C.[Fe]>[NH2:41][C:17]1[C:18]([NH:19][CH:20]2[CH2:28][CH:27]3[CH:23]([CH2:24][C:25](=[O:40])[N:26]3[CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=3[O:38][CH3:39])[CH2:22][CH2:21]2)=[C:13]2[CH:12]=[CH:11][N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:8])=[O:9])[C:14]2=[N:15][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67342802HCID 67342802, compound

Product 1

HCID 67344043HCID 67344043, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one (prepared as in Example 111) (152.3 mg, 0.2515 mmol) in ethanol (3 mL) was added ammonium chloride (59.0 mg, 1.10 mmol), iron powder (70.4 mg, 1.26 mmol), and water (5 mL). The reaction mixture was stirred at 70° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered through celite to remove iron and inorganic solids, rinsing with ethanol. The filtrate was neutralized with saturated aqueous sodium bicarbonate, and extracted twice with dichloromethane. The combined organic extracts were dried over magnesium sulphate, filtered, and evaporated in vacuo to yield 134.5 mg (93%) of 6-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-1-(2,4-dimethoxy-benzyl)-octahydro-indol-2-one, which was carried forward without purification. LCMS (Method E, ESI): RT=1.43 min, m+H=576.2.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through celite
  3. customto remove iron and inorganic solids
  4. washrinsing with ethanol
  5. extractionextracted twice with dichloromethane
  6. dry with materialThe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-836fe99cfa014118b028a5247ba3549f
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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