Diisopropylethylamine → 3-amino-N-(5-chloro-2-methylbenzyl)isoxazole-5-carboxamide

HRID 1891411ノート

反応式

HRID 1891411 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[O:4][N:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:46])=[C:42]([CH2:44][NH2:45])[CH:43]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([NH:45][CH2:44][C:42]2[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]=2[CH3:46])=[O:9])[O:4][N:3]=1

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27576735-Chloro-2-methylbenzylamineHCID 552646873-Aminoisoxazole-5-carboxylic acid

生成物 1

HCID 583322153-amino-N-(5-chloro-2-methylbenzyl)isoxazole-5-carboxamide収率 71.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-aminoisoxazole-5-carboxylic acid (492 mg, 3.84 mmol) in DMF (16 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.87 g, 4.22 mmol) at 0° C. The resulting solution was stirred for 5 min, after which time, 1-(5-chloro-2-methylphenyl)methanamine (598 mg, 3.84 mmol) and N,N-diisopropylethylamine (2.0 mL, 12 mmol) was added. The solution was stirred at room temperature for 0.5 h. The reaction solution was diluted with ethyl acetate and water, the organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was recrystallized with ethyl acetate and hexanes to give product (730 mg, 71%). LCMS calculated for C12H13ClN3O2(M+H)+: m/z=266.1.

後処理

  1. stirringThe solution was stirred at room temperature for 0.5 h
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized with ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-5dbc5b1bf85b414a913153aa730ff024
出典データセット
uspto-grants-2013_08
特許番号
US08507541B2

反応ノート

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