Tetrahydrofuran → HCID 67027148, compound

HRID 1908850Notes

Reaction equation

HRID 1908850 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:8](O)=[O:9])[CH:2]([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.CN(C(O[N:32]1[N:40]=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NN.C1COCC1>CN(C=O)C.CCOCC>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:8]([NH:32][NH2:40])=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 574372032-Methyl-6-(2-methyl-propyl)-isonicotinic acid

Product 1

HCID 67027148HCID 67027148, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-isobutyl-6-methyl-isonicotinic acid (83 mg, 0.359 mmol) and DIPEA (186 mg, 1.44 mmol) in DMF (6 mL) is added TBTU (127 mg, 0.395 mmol) at rt. The mixture is stirred for 45 min before 1 M hydrazine in THF (1.44 mL, 1.44 mmol) is added and stirring is continued for 2 h. The mixture is diluted with ether (200 mL) and washed with 1M aq. HCl (3×5 mL), 1M aq. NaOH (3×5 mL) and brine (5 mL). The org. phase is separated, dried over MgSO4, filtered and evaporated. The crude product is purified on prep. TLC plates with DCM containing 4% of methanol to give 2-isobutyl-6-methyl-isonicotinic acid hydrazide (37 mg) as a yellow oil; LC-MS: tR=0.44 min, [M+1]+=208.10.

Workup

  1. additionis added
  2. washwashed with 1M aq. HCl (3×5 mL), 1M aq. NaOH (3×5 mL) and brine (5 mL)
  3. customphase is separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-e91ac569da2543b3bd04be4301bec42e
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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