Diisopropylethylamine → HCID 68443628、化合物

HRID 1911669ノート

反応式

HRID 1911669 の反応式
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C([N:49]([CH2:53]C)[CH:50]([CH3:52])[CH3:51])(C)C.NC1C[CH2:60][O:59][CH2:58]C1>CN(C=O)C>[CH3:53][N:49]([CH:50]1[CH2:51][CH2:60][O:59][CH2:58][CH2:52]1)[C:19](=[O:21])[C:18]1[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

生成物 1

HCID 68443628HCID 68443628、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.64 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (228 mg, 0.71 mmol), N,N-diisopropyl ethyl amine (552 μL, 3.22 mmol) and 4-aminotetrahydropyran (0.77 mmol). The resulting reaction mixture was stirred for 12 h at ambient temperature. After dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 20:80) afforded the title compound (231 mg, 91%) which was obtained as a white solid. MS: m/e=394.1 [M+H]+.

後処理

  1. customThe resulting reaction mixture
  2. washAfter dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 20:80)

出典と根拠

ORDレコード
ord-51a2b68303d94d57bf4de522513ac69a
出典データセット
uspto-grants-2013_12
特許番号
US08604062B2

反応ノート

読み込み中…