Ammonium Chloride → HCID 90411101, compound

HRID 626576Notes

Reaction equation

HRID 626576 reaction equation
[CH3:1][N:2]([CH3:27])[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][C:18]3[CH:19]=[N:20][C:21]([N+:24]([O-])=O)=[CH:22][CH:23]=3)[CH:14]=[CH:13][N:12]=2)=[O:9])[CH2:4]1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:24][C:21]1[N:20]=[CH:19][C:18]([O:17][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:8]([N:5]3[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:27])[CH3:1])[CH2:4]3)=[O:9])[CH:16]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 90411230HCID 90411230, compound

Product 1

HCID 90411101HCID 90411101, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-3-(dimethylamino)-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.720 g, 1.934 mmol) in MeOH (10 mL) and THF (10 mL) was treated with NH4Cl (3.10 g, 58.0 mmol) followed by zinc dust (1.264 g, 19.34 mmol) and the mixture stirred at RT for 0.5 h. The mixture was diluted with EtOAc, the solids removed via filtration and washed with EtOAc. The filtrate was re-filtered and concentrated to dryness to afford (R)—N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-3-(dimethylamino)pyrrolidine-1-carboxamide (600 mg, 91%). MS (ESI) m/z: 343.2 (M+H+).

Workup

  1. customthe solids removed via filtration
  2. washwashed with EtOAc
  3. filtrationThe filtrate was re-filtered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a196c5eaaf9c45b8a1bee3194e224984
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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