Triethylamine → Methyl 3-[3-[3-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ureido]piperidin-1-yl]benzoate

HRID 602191ノート

反応式

HRID 602191 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:19][CH2:18][CH2:17][CH:13](C(O)=O)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C([N:39]([CH2:42]C)CC)C.[NH2:44][C:45]1[S:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)=[N:47][C:46]=1[CH3:57]>C1C=CC=CC=1.O>[Cl:56][C:53]1[CH:54]=[CH:55][C:50]([C:48]2[S:49][C:45]([NH:44][C:42](=[O:27])[NH:39][CH:13]3[CH2:17][CH2:18][CH2:19][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:3]([O:2][CH3:1])=[O:4])[CH2:12]3)=[C:46]([CH3:57])[N:47]=2)=[CH:51][CH:52]=1

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 199401P,P-Diphenylphosphinic azideHCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acidHCID 672673295-Amino-2-(4-chlorophenyl)-4-methylthiazole

生成物 1

HCID 58992627Methyl 3-[3-[3-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]ureido]piperidin-1-yl]benzoate収率 44%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

1-[3-(Methoxycarbonyl)phenyl]nipecotic acid (54.0 mg, 0.205 mmol) was suspended in benzene (4 mL). To this suspension, diphenylphosphoryl azide (0.0487 mL, 0.226 mmol) and triethylamine (0.0316 mL, 0.226 mmol) were added and the mixture was stirred for 2 hours while being refluxed. Subsequently, 5-amino-2-(4-chlorophenyl)-4-methylthiazole (46.0 mg, 0.205 mmol) and triethylamine (0.0316 mL, 0.226 mmol) were added and the mixture was further stirred for 6 hours while refluxed. Water was then added and the mixture was extracted with ethyl acetate. The extract was washed sequentially with 0.1 mol/L hydrochloric acid, a saturated aqueous sodium bicarbonate solution and brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->1:4) gave 43.5 mg (44%) of the desired compound as a yellow powder.

後処理

  1. temperaturewhile being refluxed
  2. stirringthe mixture was further stirred for 6 hours
  3. temperaturewhile refluxed
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed sequentially with 0.1 mol/L hydrochloric acid
  6. dry with materialThe washed product was dried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->1:4)

出典と根拠

ORDレコード
ord-2002cfafff2d46d2a42a0dfd9e64407f
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

読み込み中…