Diisopropylethylamine → ((2S,3R)-2-(((5-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl) (5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60914Notes

Reaction equation

HRID 60914 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[N:13]=[C:14]([CH3:24])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:11].Cl[C:26]1[O:27][C:28]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:29]=2[N:30]=1.CCN(C(C)C)C(C)C>CC#N>[F:35][C:32]1[CH:33]=[CH:34][C:28]2[O:27][C:26]([NH:1][CH2:2][C@@H:3]3[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]3[C:10]([C:12]3[N:13]=[C:14]([CH3:24])[S:15][C:16]=3[C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[O:11])=[N:30][C:29]=2[CH:31]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 141698172-Chloro-5-fluoro-1,3-benzoxazoleHCID 89739171((2S,3R)-2-(Aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Product 1

HCID 117728634((2S,3R)-2-(((5-Fluorobenzo[d]oxazol-2-yl)amino)methyl)-3-methylpiperidin-1-yl) (5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone (40 mg, 115 μmol), 2-chloro-5-fluorobenzoxazole (24 mg, 138 μmol) and DIPEA (60 μl, 345 μmol) in CH3CN (2 mL) was heated at reflux overnight. The mixture was cooled to rt and the solvent was removed in vacuo. The crude was dissolved in EtOAc and washed with satd. NaHCO3 and brine. The solvent was removed and the crude was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 483 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude was dissolved in EtOAc
  5. washwashed with satd
  6. customThe solvent was removed
  7. customthe crude was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-de2be3fe8d474bf381a2eb50d4c5f458
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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