Diisopropylethylamine → N-Hydroxy-2-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetamide

HRID 1245384노트

반응식

HRID 1245384 반응식
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH2:24][CH:23]([CH2:25][C:26]([OH:28])=O)[O:22][N:21]=3)=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.F[P-](F)(F)(F)(F)F.[N:36]1([O:45][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.NO>CN(C=O)C>[OH:45][NH:36][C:26](=[O:28])[CH2:25][CH:23]1[O:22][N:21]=[C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:19][CH:18]=2)[CH2:24]1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 21911127{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid

생성물 1

HCID 9865240N-Hydroxy-2-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetamide수율 31.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The {3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid (0.15 g, 0.4 mmol) was combined with BOP (0.265 g, 0.6 mmol) and diisopropylethylamine (0.5 mL) in DMF (5 mL) under nitrogen atmosphere at room temperature. The reaction was stirred for 15 minutes, and then hydroxylamine hydrochloride (0.042 g, 0.6 mmol) was added. The reaction was stirred overnight, concentrated in vacuo, and triturated with water saturated KH2PO4 solution to give a precipitate. The crude product was purified by HPLC on a C-18 column eluting with an acetonitrile/water/TFA gradient to give the title compound (0.05 g, 25%) as an amorphous solid. MS found: (M+H)+=392.

후처리

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated in vacuo
  3. customtriturated with water saturated KH2PO4 solution
  4. customto give a precipitate
  5. customThe crude product was purified by HPLC on a C-18 column
  6. washeluting with an acetonitrile/water/TFA gradient

출처 및 근거

ORD 기록
ord-6ccbc202c1134e9a856dc8b5b8076f2b
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125870B2

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