Boron tribromide → 3-[(5-{[(2S)-2-(4-Fluorophenyl)propyl]amino}-1,2,4-thiadiazol-3-yl)methyl]phenol

HRID 922699Notes

Reaction equation

HRID 922699 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:25])[CH2:9][NH:10][C:11]2[S:15][N:14]=[C:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=3)[N:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:25])[CH2:9][NH:10][C:11]2[S:15][N:14]=[C:13]([CH2:16][C:17]3[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 70974891(S)-N-(2-(4-fluorophenyl)propyl)-3-(3-methoxybenzyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 709747203-[(5-{[(2S)-2-(4-Fluorophenyl)propyl]amino}-1,2,4-thiadiazol-3-yl)methyl]phenolYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-(2-(4-fluorophenyl)propyl)-3-(3-methoxybenzyl)-1,2,4-thiadiazol-5-amine (80.0 mg, 0.22 mmol, 1.0 equiv) in dry DCM (5 mL) was added BBr3 (2.0 mL, 21 mmol, 1.0 equiv) by syringe. After stirring for 15 min, the reaction mixture was quenched by the addition of MeOH and the resulting mixture was concentrated in vacuo. The residue was dissolved in EtOAc and washed with sat'd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel (25% EtOAc/Hexanes) provided the title compound (24 mg, 32%). m/z=344.2 [M+H]+.

Workup

  1. customthe reaction mixture was quenched by the addition of MeOH
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with sat'd
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel (25% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c84a9a6912624ad8a0ff7a1a39cc0894
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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