Azetidine → HCID 178441332, compound

HRID 556711Notes

Reaction equation

HRID 556711 reaction equation
[C:1](Cl)(=[O:28])[O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[S:7]/[C:6]/1=[N:14]\[C:15](=[O:27])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1F.[NH:30]1[CH2:33][CH2:32][CH2:31]1>C(Cl)Cl.CO>[N:30]1([C:1]([O:2][CH2:3][CH2:4][N:5]2[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[S:7]/[C:6]/2=[N:14]\[C:15](=[O:27])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=2[N:30]2[CH2:33][CH2:32][CH2:31]2)=[O:28])[CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 2

HCID 10422AzetidineHCID 178441331HCID 178441331, compound

Product 1

HCID 178441332HCID 178441332, compoundYield 19.38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 61B (174 mg, 0.384 mmol) in CH2Cl2 (1.4 mL) was added azetidine (110 mg, 1.920 mmol) in methanol (0.5 mL) and the mixture was stirred for 2 hr. The reaction mixture was concentrated and the residue was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10-100% acetonitrile (A) and 10 mM ammonium acetate in water (B), at a flow rate of 2.0 mL/min (0-0.1 min 10% A, 0.1-2.6 min 10-100% A, 2.6-2.9 min 100% A, 2.9-3.0 min 100-10% A. 0.5 min post-run delay) to obtain the title compound (38 mg, 0.074 mmol, 19.38%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (m, 9H) 1.99-2.12 (m, 2H) 2.18-2.29 (m, 2H) 3.78 (t, J=7.29 Hz, 4H) 3.87 (t, J=7.46 Hz, 4H) 4.35 (dd, J=14.24, 4.75 Hz, 4H) 6.57 (d, J=8.82 Hz, 1H) 7.27 (s, 1H) 7.51 (dd, J=8.65, 1.86 Hz, 1H) 7.87 (d, J=1.70 Hz, 1H); MS (DCI) m/z 511 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-08e1c8b510154d6aa44b10c68fb16e3a
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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