Ammonium Chloride → HCID 66990499, compound

HRID 2407841Notes

Reaction equation

HRID 2407841 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:34]([O-])=O)[C:6]([C:12]([NH:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:24]=3)[CH2:18][CH2:17]2)=[O:13])=[N:7][C:8]=1[O:9][CH2:10][CH3:11])#[N:2].[Cl-:37].[NH4+]>O1CCCC1.C(OCC)(=O)C.O.[Zn]>[ClH:37].[NH2:34][C:5]1[C:6]([C:12]([NH:14][CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([CH2:22][C:23]3[O:27][N:26]=[C:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:24]=3)[CH2:20][CH2:21]2)=[O:13])=[N:7][C:8]([O:9][CH2:10][CH3:11])=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 66989871HCID 66989871, compound

Product 1

HCID 66990499HCID 66990499, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the compound prepared in Example 450 (120 mg) in tetrahydrofuran (2 mL) at ambient temperature was added zinc dust (160 mg), followed by saturated ammonium chloride (1 mL). The resulting mixture was stirred at ambient temperature for 17 hours. The reaction mixture was diluted with ethyl acetate and water, and then filtered through a glass filter. The filter was washed with ethyl acetate. The combined two-phase filtrate and wash were transferred to a separatory funnel and the organic layer was dried over sodium sulfate and concentrated. The residue was dissolved in methanol, and to convert to the hydrochloride salt, a 4 mol/L solution of hydrogen chloride in dioxane (0.1 mL) was added. The solvent was concentrated to provide the title compound (102 mg) with the following physical data.

Workup

  1. filtrationfiltered through a glass
  2. filtrationfilter
  3. washThe filter was washed with ethyl acetate
  4. washThe combined two-phase filtrate and wash
  5. customwere transferred to a separatory funnel
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in methanol
  9. additiona 4 mol/L solution of hydrogen chloride in dioxane (0.1 mL) was added
  10. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-7019cd52643147559f6e22f2f6d8fed5
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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