Ammonium Chloride → 4-[3,4-Diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056949Notes

Reaction equation

HRID 1056949 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)[C:3]=1[N+:34]([O-])=O.[Cl-].[NH4+]>C(OCC)(=O)C.CO.ClCCl.[Zn]>[NH2:34][C:3]1[C:4]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)=[C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 1180939284-(4-Amino-2-(cyclopropylmethoxy)-3-nitrophenyl)-6-methyl-l-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Product 1

HCID 1180939054-[3,4-Diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4-[4-amino-2-(cyclopropylmethoxy)-3-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.119 g, 0.234 mmol) in ethyl acetate (1.2 mL) and methanol (1.2 mL) was treated with saturated aqueous ammonium chloride solution (0.274 mL, 4.09 mmol). The mixture was cooled to 0° C., treated with zinc (0.122 g, 1.87 mmol) in two portions over 5 min, stirred at RT for 30 min and heated at 55° C. for 1 h. The reaction mixture was diluted with dichloromethane, filtered through a Celite pad, and the solids were washed with dichloromethane. The filtrate was concentrated to give a residue. The residue was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (20 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product that was used without further purification. LCMS calculated for C25H27N4O4S (M+H)+: m/z=479.2. found: 479.1.

Workup

  1. temperatureheated at 55° C. for 1 h
  2. filtrationfiltered through a Celite pad
  3. washthe solids were washed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customto give a residue
  6. washwashed with saturated sodium bicarbonate solution (20 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8901c283508a4f469fa34184da9d6266
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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