Isopropylamine → [2-(4-Fluorophenyl)-2-methylpropyl]{3-[(methylethyl)amino](1,2,4-thiadiazol-5-yl)}amine

HRID 922702Notes

Reaction equation

HRID 922702 reaction equation
Cl[C:2]1[N:6]=[C:5]([NH:7][CH2:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([CH3:11])[CH3:10])[S:4][N:3]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]([CH3:11])([CH3:10])[CH2:8][NH:7][C:5]2[S:4][N:3]=[C:2]([NH:22][CH:19]([CH3:21])[CH3:20])[N:6]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 709750603-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amine

Product 1

HCID 70977343[2-(4-Fluorophenyl)-2-methylpropyl]{3-[(methylethyl)amino](1,2,4-thiadiazol-5-yl)}amine

Conditions

Temperature
110 °C

Procedure

3-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amine (50 mg, 0.18 mmol, 1.0 equiv) and i-PrNH2 (0.5 mL, 5.8 mmol) were loaded into a microwave vial, and the resulting mixture was heated to 110° C. for 30 minutes. The reaction mixture was then concentrated in vacuo. Purification by silica gel (20-30% EtOAc/Hexanes) provided the title compound as an off white solid (55 mg, 99%). m/z=309.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customPurification by silica gel (20-30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-d4c586751c064995940bac88e57aa515
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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