Diisopropylethylamine → HCID 178496653, compound

HRID 1486933Notes

Reaction equation

HRID 1486933 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:21]([NH2:23])=[O:22])=[C:14]2Cl.Cl.[CH3:26][O:27][CH:28]1[CH2:31][CH:30]([NH2:32])[CH2:29]1>CC(N(C)C)=O.O>[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:21]([NH2:23])=[O:22])=[C:14]2[NH:32][C@H:30]1[CH2:31][C@@H:28]([O:27][CH3:26])[CH2:29]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 675142646-Bromo-4-chloro-3-quinolinecarboxamideHCID 722073303-Methoxycyclobutan-1-amine hydrochloride

Product 1

HCID 178496653HCID 178496653, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

DIPEA (13.76 mL, 78.80 mmol) was added to a mixture of 6-bromo-4-chloroquinoline-3-carboxamide (7.5 g, 26.27 mmol) and 3-methoxycyclobutan-1-amine hydrochloride (3.98 g, 28.89 mmol) in DMA (35 mL) and the resulting mixture stirred at 100° C. for 18 h. The reaction mixture was diluted with water (250 mL) and the precipitate was collected by filtration, washed with water (50 mL) and dried under vacuum to afford the desired material (6.28 g, 68.3%) as a tan solid, which was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 2.45-2.55 (2H, m), 2.76-2.88 (2H, m), 3.17 (3H, s), 3.66 (1H, q), 4-4.16 (1H, m), 7.67 (1H, s), 7.80 (1H, dd), 7.93 (1H, dd), 8.15 (1H, s), 8.59 (1H, s), 8.69 (1H, s), 9.34 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=350, 352.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water (50 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6dd4dfddffd046bf91a49c3f146c1264
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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