HCID 63761213, compound → HCID 67241792, compound

HRID 2422117Notes

Reaction equation

HRID 2422117 reaction equation
Cl[C:2]1[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:19][C:20]1[C:21]([N:30]2[CH2:33][CH:32]([NH2:34])[CH2:31]2)=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1>CN(C=O)C.CCOC(C)=O>[Cl:19][C:20]1[C:21]([N:30]2[CH2:31][CH:32]([NH:34][C:2]3[C:3](=[O:18])[N:4]([CH:15]([CH3:17])[CH3:16])[S:5](=[O:14])(=[O:13])[C:6]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:33]2)=[N:22][CH:23]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:25]=1

Participants

5

Reactant 2

HCID 63761213HCID 63761213, compoundHCID 672431604-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 67241792HCID 67241792, compoundYield 84,796.102%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

4-Chloro-2-isopropyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (150 mg, 0.525 mmol) was dissolved in dry DMF (1 mL) under nitrogen atmosphere. 1-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]azetidin-3-amine (133 mg, 0.530 mmol) was added followed by TEA (53 mg, 0.525 mmol) and the reaction mixture was heated in a microwave reactor for at 120° C. for 20 mins. The mixture was diluted with EtOAc, washed with saturate aqueous NaHCO3, dried with Na2SO4, filtered and evaporated. The crude product was purified on a Biotage Horizon HPFC system using Heptane and EtOAc as eluant affording the title compound (223 g, 84.0%). 1H NMR (500 MHz, CDCl3): δ 1.60 (d, 6H), 4.01-4.06 (m, 3H), 4.10-4.15 (m, 2H), 4.40-4.48 (m, 1H), 5.62 (bs, 1H), 7.51 (s, 5H), 7.59 (s, 1H), 8.25 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 20.38, 44.61, 48.06, 59.87, 109.52, 115.56, 117.98 (q, JC-F=33.6 Hz), 124.42, 124.75, 129.29, 130.48, 131.49, 134.49, 135.16, 143.70, 156.92, 158.26; Mass Spectrum: M+H+ 501.1.

Workup

  1. washwashed with saturate aqueous NaHCO3
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified on a Biotage Horizon HPFC system

Sources & evidence

ORD record
ord-96461ffd04be45b295ebae3cc721ebc4
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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