Allylamine → HCID 67437443, compound

HRID 521393Notes

Reaction equation

HRID 521393 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[CH2:10])=[N:7][S:8][C:4]=2[CH:3]=1.[CH2:20]([NH2:23])[CH:21]=[CH2:22]>CN(C=O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)[CH2:10][NH:23][CH2:20][CH:21]=[CH2:22])=[N:7][S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 7853AllylamineHCID 67437092HCID 67437092, compound

Product 1

HCID 67437443HCID 67437443, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-3-(1-(4-chlorophenyl)vinyl)benzo[d]isothiazole (600 mg, 1.71 mmol), DMF (3 mL) and allylamine (3 mL) was stirred at room temperature for 3 days. The reaction was partitioned between EtOAc and water. The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (DCM:MeOH, 20:1) to give N-(2-(6-bromobenzo[d]isothiazol-3-yl)-2-(4-chlorophenyl)ethyl)prop-2-en-1-amine (464 mg, 66%). 1H NMR (CDCl3, 400 MHz) δ □8.06 (d, J=1.6 Hz, 1H), 7.59 (d, J=8.8 Hz, 1H), 7.41 (dd, J=8.8 Hz, J=1.6 Hz, 1H), 7.25 (m, 4H), 5.86 (m, 1H), 5.16 (dd, J=17.2 Hz, J=1.6 Hz, 1H), 5.08 (d, J=10.4 Hz, 1H), 4.72 (t, J=7.2 Hz, 1H), 3.62 (dd, J=12.0 Hz, J=8.0 Hz, 1H), 3.31 (m, 2H), 3.20 (dd, J=12.0 Hz, J=6.8 Hz, 1H).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (DCM:MeOH, 20:1)

Sources & evidence

ORD record
ord-c170a85f12fe44578039e6b6c03c7077
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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