Diisopropylethylamine → HCID 67340259, compound

HRID 1675079Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:12][C:11]([F:14])([F:13])[C:8]1[N:6]2[N:7]=[C:2]([N:15]3[CH2:16][CH2:17][CH:18]([C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=5)[NH:23][CH:22]=4)[CH2:19][CH2:20]3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (1.8 g, 8.09 mmol), methyl 3-(piperidin-4-yl)-1H-indole-5-carboxylate (2.09 g, 8.09 mmol) and DIPEA (1.55 mL, 8.90 mmol) in DMF (25 mL) were stirred and heated at 80° C. for 1 hour. The resulting mixture was then cooled to ambient temperature and quenched in water (60 mL) to give a precipitate which was collected by filtration, washed sequentially with water, acetonitrile and ether and dried under vacuum to give methyl 3-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]-1H-indole-5-carboxylate (3.29 g, 92%) as a cream solid.

Workup

temperatureThe resulting mixture was then cooled to ambient temperature
customquenched in water (60 mL)
customto give a precipitate which
filtrationwas collected by filtration
washwashed sequentially with water, acetonitrile and ether
customdried under vacuum

Sources & evidence

ORD record: ord-175efd2f1010437eb88eccd2e0bbe491
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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