Cyclobutylamine → HCID 71468901, compound

HRID 1468646Notes

Reaction equation

HRID 1468646 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.[CH:16]1([NH2:20])[CH2:19][CH2:18][CH2:17]1>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:20][CH:16]1[CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 86717739HCID 86717739, compound

Product 1

HCID 71468901HCID 71468901, compoundYield 82.9%

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 cyclobutylamine (1.17 ml, 13.46 mmol) in ethanol (4 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (400 mg, 82.7%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 202° C. MS m/z (relative intensity, 70 eV) 287 (M+, 0), 260 (33), 259 (91), 216 (bp), 215 (23), 56 (73).

Workup

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

Sources & evidence

ORD record
ord-1ab1a5bc117d49458e05ed8d78b50916
Source dataset
uspto-grants-2015_04
Patent number
US09006227B2

Reaction notes

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