Dimethylformamide → HCID 68679051, compound

HRID 1173784Notes

Reaction equation

HRID 1173784 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.C(N(C(C)C)CC)(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(O)=O)=[CH:49][CH:48]=3)[CH2:43][CH2:42]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[CH3:56][N:57]([CH3:60])[CH:58]=[O:59]>>[CH3:56][N:57]([CH:60]1[CH2:15][CH2:16][CH2:11][CH2:12][N:13]1[CH3:14])[C:58](=[O:59])[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 4

HCID 6228DimethylformamideHCID 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 68679051HCID 68679051, compoundYield 44%

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 s 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-e6969702ff9847768e21dac3eedfa1ae
Source dataset
uspto-grants-2010_11
Patent number
US07834182B2

Reaction notes

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