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

HRID 1891411노트

반응식

HRID 1891411 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5dbc5b1bf85b414a913153aa730ff024
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507541B2

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