Methylamine → HCID 66549232、化合物

HRID 2174384ノート

反応式

HRID 2174384 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:28]([F:31])([F:30])[F:29])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:24][CH:23]([C:25](O)=[O:26])[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C(Cl)(=O)C(Cl)=O.[CH3:38][NH2:39]>C(Cl)Cl>[CH3:38][NH:39][C:25]([CH:23]1[CH2:24][N:21]([C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH2:11][C:10]([C:4]4[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=4)([C:28]([F:29])([F:30])[F:31])[O:14][N:13]=3)=[CH:20][CH:19]=2)[CH2:22]1)=[O:26]

参加物

5

反応物 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 86707796HCID 86707796、化合物

生成物 1

HCID 66549232HCID 66549232、化合物収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (Preparation 12, 0.1 g, 0.203 mmol) in DCM (4 mL) was added oxalyl chloride (0.030 g, 0.0.243 mmol) at 0° C. and stirred for 1 hour under nitrogen atmosphere at room temperature. After 1 hour, saturated solution of methyl amine (4 mL) was added. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was concentrated in vacuo to get crude. Crude was purified by column chromatography on silica gel (100-200 mesh). Compound was eluted using 0.7% methanol in DCM to afford pale yellow solid (0.055 g, 54%). 1H-NMR (400 MHz, CDCl3) δ: 2.86-2.90 (d, 3H, J=4.84 Hz), 3.36-3.39 (m, 1H), 3.61 (d, 1H, J=17 Hz), 4.01-4.09 (m, 5H), 5.62-5.63 (m, 1H), 6.40-6.42 (m, 2H), 7.46-7.50 (m, 2H), 7.63 (s, 2H); LC-MS (m/z): [M−H] 503.80. HPLC purity: 96.77%.

後処理

  1. waitAfter 1 hour
  2. customResulting
  3. customreaction mixture
  4. stirringwas stirred at room temperature for 16 hours
  5. customAfter complete consumption of starting material, reaction mixture
  6. concentrationwas concentrated in vacuo
  7. customto get crude
  8. customCrude was purified by column chromatography on silica gel (100-200 mesh)
  9. washCompound was eluted

出典と根拠

ORDレコード
ord-2f4c04144d934b41a47e30a40a1a22ce
出典データセット
uspto-grants-2015_06
特許番号
US09061013B2

反応ノート

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