Diisopropylethylamine → HCID 59149841, compound

HRID 1675005Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (251 mg, 1.13 mmol), (R)-1-[1-(4-bromophenyl)ethyl]piperazine (obtained as described in Example 270, preparation of starting materials, 304 mg, 1.13 mmol) and DIPEA (0.20 mL, 1.13 mmol) in DMF (3 mL) were stirred and heated at 80° C. for 1 hour. The resulting solution was cooled to ambient temperature then quenched with water (10 mL) to give a pale brown precipitate. The precipitate was collected by filtration, washed sequentially with water, acetonitrile and ether and dried under vacuum to afford 6-[4-[(1R)-1-(4-bromophenyl)ethyl]piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (437 mg, 85%) as a pale brown solid.

Workup

temperatureThe resulting solution was cooled to ambient temperature
customthen quenched with water (10 mL)
customto give a pale brown precipitate
filtrationThe precipitate was collected by filtration
washwashed sequentially with water, acetonitrile and ether
customdried under vacuum

Sources & evidence

ORD record: ord-a6688a097ad44f66b109c6098390cbad
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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