Allylamine → HCID 67437443, compound

HRID 2192456Notes

Reaction equation

HRID 2192456 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-2f78b26d09ef48f2a865099955602cf5
Source dataset
uspto-grants-2012_12
Patent number
US08329709B2

Reaction notes

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