Methanol → N,N-Dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxamide

HRID 2046920Notes

Reaction equation

HRID 2046920 reaction equation
Cl.[CH3:2][C:3]1([CH3:21])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH:11]=[N:12][N:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:14]=2)[O:4]1.CCN(C(C)C)C(C)C.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34].CO>CN(C=O)C>[CH3:31][N:32]([CH3:36])[C:33]([N:18]1[CH2:19][CH2:20][CH:15]([N:13]2[CH:14]=[C:10]([B:5]3[O:6][C:7]([CH3:8])([CH3:9])[C:3]([CH3:21])([CH3:2])[O:4]3)[CH:11]=[N:12]2)[CH2:16][CH2:17]1)=[O:34]

Participants

6

Reactant 4

HCID 887MethanolHCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 667591824-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

Product 1

HCID 67365794N,N-Dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine hydrochloride (253.6 mg, 0.809 mmol) in DMF (6 mL), DIPEA (0.7 mL, 4 mmol) was added at rt. The solution was cooled to 0° C. and N,N-dimethylcarbamoyl chloride (107.7 mg, 1.002 mmol) in DMF (1 mL) was added. The reaction was stirred from 0° C.→rt for 30 min. MeOH was added and all organic solvent was concentrated in vacuo to dryness. The residue was dissolved in CH2Cl2, washed once with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title compound as a waxy white solid that solidified upon drying. The material was used without further purification. 1H NMR (400 MHz, CDCl3): δ=1.32 (s, 12H), 1.94-2.07 (m, 2H), 2.16 (dd, J=12.3, 2.4 Hz, 2H), 2.85 (s, 6H), 2.87-2.95 (m, 2H), 3.78 (d, J=13.4 Hz, 2H), 4.24-4.34 (m, 1H), 7.76 (s, 1H), 7.80 (s, 1H). MS (AP+): m/z 349.13 (100) [MH+]. HPLC: tR=2.91 min (ZQ3, polar—5 min).

Workup

  1. concentrationall organic solvent was concentrated in vacuo to dryness
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed once with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a5308d42b0741d7a70713137f3df47a
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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