Diisopropylethylamine → 6-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

HRID 1675028Notes

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](=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:23]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:29]2[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([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)[CH2:16][CH2:17]2)=[CH:22]1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (160 mg, 0.72 mmol), 3-(piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine (145 mg, 0.72 mmol) and DIPEA (0.14 mL, 0.79 mmol) in DMF (2.0 mL) were stirred and heated at 80° C. for 1 hour. The resulting mixture was then cooled to ambient temperature and quenched in water (10 mL) to give a beige solid. The solid was collected by filtration, washed sequentially with water, acetonitrile and ether, and air dried to give 6-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (217 mg, 78%) as a colourless solid.

Workup

temperatureThe resulting mixture was then cooled to ambient temperature
customquenched in water (10 mL)
customto give a beige solid
filtrationThe solid was collected by filtration
washwashed sequentially with water, acetonitrile and ether, and air
customdried

Sources & evidence

ORD record: ord-22b51d7e63894ce9b355f4de9f9657e7
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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