Acetic Acid → HCID 136501887, compound

HRID 706792Notes

Reaction equation

HRID 706792 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:18][C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][N:15]3[N:14]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-].[C:23]([OH:26])(=[O:25])C.Cl>C1COCC1.[Zn]>[CH:23]([OH:26])=[O:25].[NH2:1][C:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[NH:18][C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][N:15]3[N:14]=2)=[CH:11][CH:12]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 136501883HCID 136501883, compound

Product 1

HCID 136501887HCID 136501887, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-[4-(1-azido-1-methyl-ethyl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]-triazin-4-one (115 mg, 0.39 mmol) in 2 ml THF are added zinc dust (128 mg, 1.96 mmol) and acetic acid (225 μl, 3.93 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. The mixture is filtered with suction. The filtrate is washed with saturated sodium carbonate solution and saturated sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The residue is purified by preparative HPLC to afford 2-[4-(1-amino-1-methyl-ethyl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one formate salt as white solid; HPLC/MS 1.25 min (C), [M-NH2]+ 252;

Workup

  1. filtrationThe mixture is filtered with suction
  2. washThe filtrate is washed with saturated sodium carbonate solution and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-6368f7e3db684ce69edc07be3a599554
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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