Methyl N-(triethylammoniosulfonyl)carbamate → HCID 58329498, compound

HRID 1043865Notes

Reaction equation

HRID 1043865 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1)=[O:7])(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>CN(C)C=O.O1CCCC1>[C:8]1([C:6]2[O:7][C:1]([CH3:2])=[N:4][N:5]=2)[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 58329558HCID 58329558, compound

Product 1

HCID 58329498HCID 58329498, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

N′-acetyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbohydrazide was dissolved in 0.8 mL of mixture of N,N-dimethylformamide/tetrahydrofuran (9:1). To the solution was added Burgess Reagent (120 mg, 500 μmol). The reaction was heated at 120° C. for 24 hours. The solvent was removed under reduced pressure. residues were purified The crude product was purified using reverse phase chromatography (HPLC, C-18) using trifluoroacetic acid as a modifier to give 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-5-methyl-1,3,4-oxadiazole (56) as a yellow solid. Mp=70-72° C.; 400 MHz 1HNMR (DMSO-d6) δ 8.01 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 7.15 (t, J=7.6 Hz, 1H), 7.02 (d, J=7.2 Hz, 1H), 4.27 (t, J=5.6 Hz, 2H), 2.97 (t, J=6.0 Hz, 2H), 2.56 (s, 3H), 2.18-2.14 (m, 2H); LCMS [M+H]: 240.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customresidues were purified The crude product
  3. customwas purified

Sources & evidence

ORD record
ord-db3bb91b40074dffae7acec87b373abb
Source dataset
uspto-grants-2013_10
Patent number
US08563567B2

Reaction notes

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