HCID 67123706, compound → HCID 67124182, compound

HRID 1843131Notes

Reaction equation

HRID 1843131 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[CH:10][C:11]([C:12]3[N:20]=[C:19]4[C:15]([NH:16][C:17](=[O:26])[N:18]4[C@H:21]([CH3:25])[C:22](O)=[O:23])=[CH:14][N:13]=3)=[C:5]2[CH:4]=1)#[N:2]>C1COCC1>[OH:23][CH2:22][C@H:21]([N:18]1[C:17](=[O:26])[NH:16][C:15]2[C:19]1=[N:20][C:12]([C:11]1[CH:10]=[N:9][N:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=13)=[N:13][CH:14]=2)[CH3:25]

Participants

3

Reactant 1

HCID 67123706HCID 67123706, compound

Product 1

HCID 67124182HCID 67124182, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of example 14 (60 mg, 0.17 mmol) in THF (10 mL) at 0° C., 1 M THF borane complex solution in THF (0.69 mL, 0.69 mmol) was added. The reaction mixture was stirred at room temperature overnight, quenched with MeOH (10 mL) and the reaction mixture was evaporated under reduced pressure. The crude residue was cromatographed on a silica gel flash system (ISCO Combiflash) using CH2Cl2/MeOH mixtures of increasing polarity as eluent to afford 4 mg of the desired product (7% yield).

Workup

  1. customquenched with MeOH (10 mL)
  2. customthe reaction mixture was evaporated under reduced pressure
  3. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-aa8122a412804c778fd5c2280cfa0a0d
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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