Diisopropylethylamine → HCID 59149816, compound

HRID 1675049Notes

Reaction equation

CCN(C(C)C)C(C)C.[CH3:10][NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][N:26]=3)[N:23]=2)[CH2:14][CH2:13]1.Br.Br[CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1>CC(N(C)C)=O>[CH3:10][N:11]([CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)[CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([C:27]([F:30])([F:28])[F:29])=[N:25][N:26]=3)[N:23]=2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 150 °C

Procedure

DIPEA (0.174 mL, 1.00 mmol) was added to N-methyl-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-amine (100 mg, 0.34 mmol) and 3-(bromomethyl)pyridine hydrobromide (127 mg, 0.50 mmol) in DMA (2 mL) and the mixture was sealed into a microwave tube. The reaction was heated to 150° C. for 15 minutes in the microwave reactor and cooled to ambient temperature. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-methyl-N-(pyridin-3-ylmethyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-amine (113 mg, 78%) as a solid.

Workup

customthe mixture was sealed into a microwave tube
temperaturecooled to ambient temperature
customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 30 mm diameter, 100 mm length)
additionFractions containing the desired compound
customwere evaporated to dryness

Sources & evidence

ORD record: ord-f3a6a7c890034a3881e2e3b1dbeecb2a
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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