Acetic Acid → HCID 59149767, compound

HRID 1675130Notes

Reaction equation

HRID 1675130 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:35])([F:34])[C:12]1[N:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=4)[NH2:30])[CH2:23][CH2:22]3)[CH:19]=[CH:20][C:15]2=[N:14][N:13]=1.[C:36](O)(=[O:38])[CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O>[F:35][C:11]([F:10])([F:34])[C:12]1[N:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[C:29]([NH:30][C:36](=[O:38])[CH3:37])[CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)[CH:19]=[CH:20][C:15]2=[N:14][N:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59149829HCID 59149829, compound

Product 1

HCID 59149767HCID 59149767, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

DIPEA (123 μl, 0.70 mmol) was added to 3-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]aniline (obtained as described in Example 616) (85 mg, 0.23 mmol), acetic acid (16 μl, 0.28 mmol) and HATU (107 mg, 0.28 mmol) in DMA (2 mL). The resulting solution was stirred at ambient temperature for 2 hours then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and acetonitrile as eluents. Fractions containing the desired compound were evaporated to dryness to give N-[3-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]acetamide (89 mg, 94%) as a solid.

Workup

  1. customthen purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-4715993968d24d969c29a25023f867dd
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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