Triethylamine → {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

HRID 2363356Notes

Reaction equation

HRID 2363356 reaction equation
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].C(N(CC)CC)C>C(Cl)Cl.Cl.O1CCOCC1>[CH3:27][C:22]1([CH3:28])[C:23]([CH3:25])([CH3:26])[O:24][B:20]([C:18]2[CH:17]=[N:16][N:15]([C:4]3([CH2:3][C:1]#[N:2])[CH2:5][NH:6][CH2:7]3)[CH:19]=2)[O:21]1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 67457197tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 71143620{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrileYield 85%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 3-(cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (1.5 g, 3.9 mmol) (Example 40, Step 1) in methylene chloride (15 mL) and 4.0 M hydrogen chloride in dioxane (3.9 mL) was stirred at room temperature over weekend. The mixture was treated with triethylamine (1 mL), and the volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%) to afford the desired product (0.95 g, 85%). LCMS (M+H)+: m/z=289.2.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%)

Sources & evidence

ORD record
ord-ebf4a355fb914cd5a541ee399d38f8a5
Source dataset
uspto-grants-2014_04
Patent number
US08691807B2

Reaction notes

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