2-Butanamine, 2-methyl- → HCID 70979663, compound

HRID 1468645Notes

Reaction equation

HRID 1468645 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([F:15])[CH:6]=1.[C:16]([NH2:21])([CH2:19][CH3:20])([CH3:18])[CH3:17]>C(O)C>[F:15][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=1)[O:4][CH2:3][CH2:2][NH:21][C:16]([CH3:18])([CH2:19][CH3:20])[CH3:17]

Participants

4

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 86717739HCID 86717739, compound

Product 1

HCID 70979663HCID 70979663, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and tert-amylamine (1.61 ml, 13.46 mmol) in ethanol (5 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (389 mg, 76.2%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 190.2° C. MS m/z (relative intensity, 70 eV) 303 (M+, 0), 288 (21), 276 (10), 275 (41), 274 (bp), 84 (10).

Workup

  1. customPreparation
  2. customPurification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15)

Sources & evidence

ORD record
ord-284f8f8c6e3c49c3bece7195a48f9cbb
Source dataset
uspto-grants-2015_04
Patent number
US09006227B2

Reaction notes

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