4-Cyanobenzoic acid → HCID 57345433, compound

HRID 1808849Notes

Reaction equation

HRID 1808849 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:43]1([C@H:49]([NH:56][CH3:57])[CH2:50][N:51]2[CH2:54][CH:53]([OH:55])[CH2:52]2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:56]([C@@H:49]([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH2:50][N:51]2[CH2:52][CH:53]([OH:55])[CH2:54]2)[CH3:57])=[O:9])=[CH:10][CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 120874-Cyanobenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67773410HCID 67773410, compound

Product 1

HCID 57345433HCID 57345433, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-cyanobenzoic acid (65.0 mg, 0.44 mmol) in DCM (2 mL) was treated with DIPEA (0.231 mL, 1.32 mmol) and TBTU (142 mg, 0.44 mmol) and the suspension was stirred for 10 min. A 125 mg/mL solution of (S)-1-(2-cyclohexyl-2-(methylamino)ethyl)azetidin-3-ol (Compound G2.3) (125 mg, 0.44 mmol) in DCM (1 mL) was added and the reaction was stirred at ambient temperature overnight. The reaction was washed with 8% aq. sol. of NaHCO3 and concentrated. The residue was dissolved in DMSO (0.4 mL) and filtered through a syringe filter. The residue was purified by HPLC to give the title compound (73.6 mg, 49%). Mixture of rotamers. 1H NMR (600 MHz, DMSO-d6) δ 0.53-0.70, 0.89-1.81, 2.43-2.59, 2.64-2.78, 3.03, 3.28-3.31, 3.43-3.54, 4.11-4.30, 5.23, 5.26, 7.48, 7.61, 7.87-7.94. HRMS (M+H)+: calculated 342.2181. found 342.2193

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. washThe reaction was washed with 8% aq. sol. of NaHCO3
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in DMSO (0.4 mL)
  5. filtrationfiltered through a syringe
  6. filtrationfilter
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-20e6240c5bd34d8b9af0b1b047d6edae
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

Loading…