Triethylamine → HCID 89995593, compound

HRID 523094Notes

Reaction equation

HRID 523094 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[C:29]([OH:31])=O.C(N(CC)CC)C.Cl.[CH3:46][O:47][CH:48]1[CH2:51][NH:50][CH2:49]1>ClCCl>[OH:25][C:26]1[CH:27]=[C:28]([C:29]([N:50]2[CH2:51][CH:48]([O:47][CH3:46])[CH2:49]2)=[O:31])[CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 692653-Hydroxy-4-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222428583-Methoxyazetidine hydrochloride

Product 1

HCID 89995593HCID 89995593, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (2.1 g, 5.5 mmol) was added to a solution of 3-hydroxy-4-nitrobenzoic acid (915 mg, 5 mmol), triethylamine (1.1 g, 11 mmol)) and 3-methoxyazetidine hydrochloride (740 mg, 5.5 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 30 minutes. The reaction was partitioned between EtOAc (30 mL) and water (30 mL). The organic phase was collected, washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a gradient of 100% ethyl acetate to 3% methanol in ethyl acetate to afford the title compound as a pale yellow solid (830 mg, 66%).

Workup

  1. customThe reaction was partitioned between EtOAc (30 mL) and water (30 mL)
  2. customThe organic phase was collected
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a gradient of 100% ethyl acetate to 3% methanol in ethyl acetate

Sources & evidence

ORD record
ord-6676839c5fe3482b914b142b7c9f4db3
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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