Acetic Acid → HCID 90038832, compound

HRID 2207335Notes

Reaction equation

HRID 2207335 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([F:23])[CH:17]=3)=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].C(O)(=O)C.[ClH:29].CO>C1COCC1.[Zn]>[ClH:29].[NH2:1][C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:24])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([F:23])[CH:17]=3)=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 90040127HCID 90040127, compound

Product 1

HCID 90038832HCID 90038832, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3-[4-(1-azido-1-methyl-ethyl)-phenyl]-7-fluoro-2H-isoquinolin-1-one (141 mg, 0.44 mmol) in 4 ml THF are added zinc dust (143 mg, 2.19 mmol) and acetic acid (250 μl, 4.37 mmol) and the mixture is stirred for 18 hours at room temperature. The suspension is diluted with THF and acidified with a small amount of 25% hydrochloric acid to obtain a clear solution. More THF and methanol are added. The mixture is filtered and the filtrate is evaporated. The residue is triturated with water, the solids are filtered off, washed with water and dried under vacuum to afford 3-[4-(1-amino-1-methyl-ethyl)-phenyl]-7-fluoro-2H-isoquinolin-1-one hydrochloride as white solid;

Workup

  1. customto obtain a clear solution
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is triturated with water
  5. filtrationthe solids are filtered off
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-04ace61bbdce40d59e88baac574f2d06
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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