Bromocyclopentane → HCID 11647540, compound

HRID 2239612Notes

Reaction equation

HRID 2239612 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:6]1(=[O:29])=[O:28])([CH3:4])(C)[CH3:2].Br[CH:31]1CCC[CH2:32]1>C(O)(C(F)(F)F)=O>[CH:1]1([N:5]2[C:9](=[O:10])[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:6]2(=[O:29])=[O:28])[CH2:2][CH2:32][CH2:31][CH2:4]1

Participants

4

Reactant 2

HCID 8728BromocyclopentaneHCID 114952832-tert-Butyl-5-phenyl-4-[(4-phenylbutyl)amino]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11647540HCID 11647540, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

2-tert-Butyl-5-phenyl-4-[(4-phenylbutyl)amino]isothiazol-3(2H)-one 1,1-dioxide (Example 1) (0.150 g, 0.364 mmol) was dissolved in TFA (3 mL) and heated in a microwave reactor at 120° C. for 20 mins. TFA was removed in vacuo and the residue was coevaporated with DCM two times. The residue was dissolved in MeCN (3 mL) and it was mixed with bromocyclopentan (0.162 g, 1.09 mmol) and TEA (0.110 g, 1.09 mmol) and the mixture was heated in a microwave reactor at 120° C. for 20 mins, at 160° C. for 85 mins and at 170° C. for 20 mins. The residue was purified by column chromatography (Horizons Biotage) using a 90:10 mixture of hexane and EtOAc as eluant, to give the title compound (0.055 g, 36%); 1H NMR (500 MHz, CDCl3): δ 7.53-7.48 (m, 2H), 7.46-7.41 (m, 3H), 7.31-7.25 (m 2H), 7.22-7.18 (m, 1H), 7.10-7.06 (m, 2H), 5.30-5.24 (br m, 1H), 4.41-4.35 (m, 1H), 2.90-2.83 (m 2H), 2.49-2.43 (m 2H), 2.25-2.17 (m 2H), 2.18-2.09 (m 2H), 1.97-1.87 (m 2H), 1.69-1.60 (m 2H), 1.44-1.36 (m 4H); 13C NMR (125 MHz, CDCl3): δ 159.0, 141.8, 135.6, 131.8, 129.8, 128.8, 128.6, 128.5, 126.2, 125.3, 106.7, 55.2, 44.2, 35.4, 29.5, 29.2, 28.3, 24.3.

Workup

  1. customTFA was removed in vacuo
  2. dissolutionThe residue was dissolved in MeCN (3 mL)
  3. temperaturethe mixture was heated in a microwave reactor at 120° C. for 20 mins, at 160° C. for 85 mins and at 170° C. for 20 mins
  4. customThe residue was purified by column chromatography (Horizons Biotage)
  5. additiona 90:10 mixture of hexane and EtOAc as eluant

Sources & evidence

ORD record
ord-201c701152c14753ba669eb9584878c0
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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