Triethylamine → HCID 13352720, compound

HRID 1186683Notes

Reaction equation

HRID 1186683 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7](O)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.F[P-](F)(F)(F)(F)F.[N:23]1([O:32][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.NO.C(N(CC)CC)C>N1C=CC=CC=1.C(Cl)Cl>[OH:32][NH:23][C:7]([C:2]1[C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70357o-Phenylbenzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 13352720HCID 13352720, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-biphenylcarboxylic acid 1 (0.25 g, 1.261 mmol), BOP (0.558 g, 1.261 mmol), hydroxylamine hydrochloride (0.088 g, 1.261 mmol) and triethylamine (0.527 mL, 3.78 mmol) was stirred in pyridine (5 mL) at room temperature overnight then diluted with DCM, washed with water (2×), dried over MgSO4, filtered and solvent evaporated to provide title compound 2 (8.8 mg, 3% yield) as a white solid after purification by Biotage (50 to 100% EtOAc in Hexane) followed by trituration (Et2O). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.77 (s, 1H), 8.97 (s, 1H), 7.52 to 7.42 (m, 1H), 7.40 to 7.33 (m, 8H). LRMS (ESI): (calc.) 213.23 (found) 214.2 (MH)+

Workup

  1. washwashed with water (2×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-3b60f4b32a6344baa7c24487722bf619
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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