Triethylamine → HCID 58329558, compound

HRID 1043864Notes

Reaction equation

[C:1]1([C:13]([OH:15])=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[C:47]([NH:50][NH2:51])(=[O:49])[CH3:48]>CN(C)C=O>[C:47]([NH:50][NH:51][C:13]([C:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1)=[O:15])(=[O:49])[CH3:48]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (20 mg, 100 μmol) in dry N,N-dimethylformamide (700 μL) were added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (42 mg, 110 μmol), triethylamine (21 μL, 150 μmol), and acetohydrazide (10 μmol). The reaction was heated at 80° C. for 24 hours. The solvent was removed under reduced pressure. To the residue were added 1.5 mL of mixture of butanol and 1,2-dichloroethane (1:2.5) and 1.0 mL of sat. NaHCO3. The organic layer was separated and the solvent was removed under reduced pressure to afford N′-acetyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carbohydrazide (55). The crude was used for the next step without further purification.

Workup

customThe solvent was removed under reduced pressure
additionTo the residue were added 1.5 mL of mixture of butanol and 1,2-dichloroethane (1:2.5) and 1.0 mL of sat. NaHCO3
customThe organic layer was separated
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-d1edf2c9c44b465a940264d2d3f33f53
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563567B2

Reaction notes

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