Tetrahydrofuran → HCID 3329081, compound

HRID 1477752Notes

Reaction equation

HRID 1477752 reaction equation
CN(C(O[N:9]1[N:17]=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28].CCN(C(C)C)C(C)C.NN.C1COCC1>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:25]([CH3:33])=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH:9][NH2:17])=[O:28]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 820103-Chloro-2-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 3329081HCID 3329081, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

TBTU (678 mg, 2.11 mmol) was added to a rt solution of 3-chloro-2-methylbenzoic acid (300 mg, 1.76 mmol) and DIPEA (0.9 mL, 5.28 mmol) in DMF (5.0 mL) and the resulting solution was stirred at rt for 15 min. The mixture was cooled to 0° C. and 1M hydrazine in THF (10.6 mL, 10.6 mmol) was added and the yellow solution was stirred at rt overnight. The rxn mixture was diluted with DCM and washed with sat. aq. NaHCO3. The aq. layer was re-extracted with DCM (1×) and the combined org. layers were concentrated in vacuo to give the title compound D-1-2 as a light orange solid that was used further without purification. LC-MS A: tR=0.50 min; [M(35Cl)+H]+=185.24.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringthe yellow solution was stirred at rt overnight
  3. washwashed with sat. aq. NaHCO3
  4. extractionThe aq. layer was re-extracted with DCM (1×)
  5. concentrationlayers were concentrated in vacuo

Sources & evidence

ORD record
ord-ef0b4c3af39f494cb470666f3429a965
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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