2,4-Dichlorobenzoic Acid → HCID 67775367, compound

HRID 1808814Notes

Reaction equation

HRID 1808814 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[N:41]1([CH2:45][C@@H:46]([NH:50][CH3:51])[CH2:47][CH2:48][CH3:49])[CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[N:41]1([CH2:45][C@@H:46]([N:50]([CH3:51])[C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=2[Cl:1])[CH2:47][CH2:48][CH3:49])[CH2:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 57872,4-Dichlorobenzoic AcidHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67773374HCID 67773374, compound

Product 1

HCID 67775367HCID 67775367, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Dichlorobenzoic acid (92 mg, 0.48 mmol) and TBTU (162 mg, 0.50 mmol) was mixed in DMF (1.5 mL). The mixture was cooled to 0° C. and NMM (0.063 mL, 0.58 mmol) was dropwise added. After 10 min at 0° C. was (S)-1-(azetidin-1-yl)-N-methyl-pentan-2-amine (Compound J1) (75 mg, 0.48 mmol) added. The resultant mixture was stirred at 0° C. for 30 min and at rt for 16 h. The mixture was concentrated and the residue dissolved in DCM (5 mL). The organic phase was washed with NaHCO3 (saturated, 2×5 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (98 mg, 62%). Mixture of rotamers: 1H NMR (400 MHz, DMSO-d6): 0.59-0.87, 0.90, 0.98-1.66, 1.72-2.11, 2.22-2.47, 2.5, 2.78, 4.26-4.70, 7.24-7.36, 7.43-7.64, 7.65-7.79. Total no of protons: 22. HRMS (M+H)+: calculated 329.1187. found 329.1161

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in DCM (5 mL)
  3. washThe organic phase was washed with NaHCO3 (saturated, 2×5 mL)
  4. filtrationfiltered through a phase separator
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-fb1ae383bad141ab8f7f450303d1e26b
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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