Diisopropylethylamine → HCID 11361527, compound

HRID 1985598Notes

Reaction equation

HRID 1985598 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2[N:13]=[CH:14]C=CC=2N=N1.[CH:25]([N:28]([CH:31]([CH3:33])C)[CH2:29][CH3:30])(C)C.Cl.[N:35]1([CH:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:55]=[CH:54][C:50]([C:51]([OH:53])=O)=[CH:49][CH:48]=3)[CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C)C=O>[CH3:12][N:13]([CH:14]1[CH2:30][CH2:29][N:28]([CH3:25])[CH2:31][CH2:33]1)[C:51](=[O:53])[C:50]1[CH:49]=[CH:48][C:47]([N:44]2[CH2:43][CH2:42][CH:41]([N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH2:46][CH2:45]2)=[CH:55][CH:54]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66779499HCID 66779499, compound

Product 1

HCID 11361527HCID 11361527, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 1-methyl(4-methylamino)piperidine (0.056 ml, 0.38 mmols), O-(7-azabenzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (121 mg, 0.32 mmols) and diisopropylethylamine (0.17 ml, 0.96 mmols) were added to a dimethylformamide solution (1.0 ml) of 4-[(4-piperidin-1-yl)piperidin-1-yl]benzoic acid hydrochloride (103 mg, 0.32 mmols) obtained in Reference Example 1, and stirred in a nitrogen atmosphere at room temperature for 14 hours. The reaction solution was extracted with ethyl acetate, the organic layer was washed with water, saturated sodium bicarbonate solution and saturated saline solution in the order, dried with anhydrous magnesium sulfate, and then concentrated. The residue was purified through preparative thin-layer chromatography (chloroform/methanol/aqueous ammonia=10/1/0.1) to obtain the entitled compound (56 mg, 44%).

Workup

  1. customobtained in Reference Example 1
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washthe organic layer was washed with water, saturated sodium bicarbonate solution and saturated saline solution in the order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified through preparative thin-layer chromatography (chloroform/methanol/aqueous ammonia=10/1/0.1)

Sources & evidence

ORD record
ord-77fc7612e5fc45d8bc182520b1cc7f64
Source dataset
uspto-grants-2009_06
Patent number
US07547693B2

Reaction notes

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