Dimethylamine → HCID 59149740, compound

HRID 1675067Notes

Reaction equation

HRID 1675067 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][O:19][CH2:20][C:21](OC)=[O:22])[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.CO.[CH3:29][NH:30][CH3:31]>>[CH3:29][N:30]([CH3:31])[C:21](=[O:22])[CH2:20][O:19][CH2:18][CH:15]1[CH2:14][CH2:13][N:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:25])([F:26])[F:1])=[N:4][N:5]=3)[N:8]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 67341254HCID 67341254, compound

Product 1

HCID 59149740HCID 59149740, compoundYield 48.8%

Procedure

A stirred solution of methyl 2-[[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]methoxy]acetate (95 mg, 0.25 mmol) in 2M dimethylamine in methanol (2.0 mL, 4.00 mmol) was heated at 120° C. in a microwave reactor for 1 hour. The reaction mixture was evaporated and the crude product was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 19 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,N-dimethyl-2-[[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]methoxy]acetamide (48.0 mg, 48.8%) as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude product was purified by preparative LCMS (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  3. additionFractions containing the desired compound
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-58b709e056dc4dc2bcaf3b810b2c10c9
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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