Diethylamine → HCID 44537865, compound

HRID 1908954Notes

Reaction equation

HRID 1908954 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]2[N:16]=[N:17][C:18]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[C:4]2[N:3]=1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>CN(C=O)C>[CH2:28]([N:30]([CH2:31][CH3:32])[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]2[N:16]=[N:17][C:18]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[C:4]2[N:3]=1)[CH3:29]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86662380HCID 86662380, compound

Product 1

HCID 44537865HCID 44537865, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-chloro-7,8-dimethoxy-3-(phenylsulfonyl)-[1,2,3]triazolo[1,5-a]quinazoline (25 mg, 0.062 mmol) and diethylamine (32 uL, 0.31 mmol) in DMF (2 mL) was heated at 40° C. for 1.5 hrs. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate in hexane to yield the desired product (22 mg, 82%). 1H NMR (CDCl3, 600 MHz) δ 8.23 (d, 2H, J=7.2 Hz), 7.93 (s, 1H), 7.55-7.52 (m, 1H), 7.49-7.57 (m, 2H), 7.32 (s, 1H), 4.10 (s, 3H), 3.99 (s, 3H), 3.76 (q, 4H, J=7.2 Hz), 1.46 (t, 6H, J=7.2 Hz); MS (ES+) m/z 442.1 (M+H)+

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f4b73d0b574f4fde9d80363aa9ff412c
Source dataset
uspto-grants-2013_12
Patent number
US08598342B2

Reaction notes

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