Ammonium Chloride → HCID 86279157, compound

HRID 576731Notes

Reaction equation

HRID 576731 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:3]=1[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]=3)=[N:13][N:14]=[C:7]2[C:6]1=[O:21].[Cl-].[NH4+]>CC(C)=O.O.[Zn]>[NH2:26][C:23]1[CH:24]=[CH:25][C:2]([Cl:1])=[C:3]([CH:22]=1)[CH2:4][N:5]1[C@@H:10]([CH3:11])[CH2:9][N:8]2[C:12]([C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]=3)=[N:13][N:14]=[C:7]2[C:6]1=[O:21]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86279093HCID 86279093, compound

Product 1

HCID 86279157HCID 86279157, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of Example 90 (20 mg, 0.05 mmol) in acetone (0.4 mL) and water (0.1 ml) was added zinc dust (33 mg, 0.5 mmol) followed by ammonium chloride (27 mg, 0.5 mmol) and the reaction mixture was stirred for 10 minutes. The reaction mixture was filtered through a pad of celite, extracted with DCM and the organic layers were collected. The organic layers were washed with brine, dried with Na2SO4, filtered, concentrated and purified by reverse-phase HPLC to provide the desired compound (5 mg, 27%). MS (ESI): mass calcd. for C17H16ClN7O, 369.8; m/z found, 370.2 [M+H]+. 1H NMR (400 MHz, DMSO) δ 9.48 (d, J=1.2 Hz, 1H), 8.87-8.79 (m, 2H), 7.15 (d, J=8.5 Hz, 1H), 6.74 (s, 1H), 6.59 (d, J=8.4 Hz, 1H), 5.06 (d, J=16.3 Hz, 1H), 4.96 (d, J=11.9 Hz, 1H), 4.81-4.68 (m, 1H), 4.34 (d, J=16.1 Hz, 1H), 4.06 (s, 1H), 1.17 (d, J=6.7 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. extractionextracted with DCM
  3. customthe organic layers were collected
  4. washThe organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-50ab89d537f043b1819cdba288a50544
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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