Acetic Acid → HCID 89826997, compound

HRID 2272980Notes

Reaction equation

HRID 2272980 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:23])[C:16]3[N:17]([CH:19]=[C:20]([F:22])[CH:21]=3)[CH:18]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].[C:24]([OH:27])(=[O:26])C>C1COCC1.[Zn]>[CH:24]([OH:27])=[O:26].[NH2:1][C:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:14][C:15](=[O:23])[C:16]3[N:17]([CH:19]=[C:20]([F:22])[CH:21]=3)[CH:18]=2)=[CH:11][CH:12]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89826370HCID 89826370, compound

Product 1

HCID 89826997HCID 89826997, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 103 mg (0.33 mmol) 3-[4-(1-azido-1-methyl-ethyl)-phenyl]-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one and 90 mg (1.38 mmol) zinc dust in 2 ml THF is added 175 ml (3.1 mmol) acetic acid and the mixture is stirred for 3 hours at room temperature. The suspension is quenched with THF/dichloromethane/ethyl acetate. The mixture is filtered with suction and the residue is washed with methanol. The filtrate is evaporated and the residue is purified by preparative HPLC to afford 3-[4-(1-amino-1-methyl-ethyl)-phenyl]-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one formate salt as white solid; HPLC/MS 1.57 min (B), [M+H] 268;

Workup

  1. customThe suspension is quenched with THF/dichloromethane/ethyl acetate
  2. filtrationThe mixture is filtered with suction
  3. washthe residue is washed with methanol
  4. customThe filtrate is evaporated
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-84f2dbc75fa842e588161042dba8c2bc
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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