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Triethylamine → 3-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 1663155
ノート
印刷プレビュー

反応式

HRID 1663155 の反応式
[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(N(CC)CC)C.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.Cl.[CH3:50][C:51]1[S:52][CH:53]=[C:54]([CH2:56][O:57][NH2:58])[N:55]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:58][O:57][CH2:56][C:54]1[N:55]=[C:51]([CH3:50])[S:52][CH:53]=1)=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 54606663HCID 54606663、化合物HCID 589898483-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid

生成物 1

HCID 112228443-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

3-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid (200 mg, see preparation 1D) was dissolved in DMF (20 ml) and triethylamine (0.65 ml) at 50-60° C. N,N,N′,N′-Tetramethyl-O-(benzotriazole-1-yl)uronium-tetrafluoroborate (250 mg) was added and after 5 minutes O-(2-methyl-thiazol-4-ylmethyl)-hydroxylamine hydrochloride (209 mg, see preparation 12) was added. The reaction mixture was heated to 90° C. and stirred at this temperature for 2 hours. The mixture was cooled to room temperature and water was added. The mixture was extracted several times with EtOAc and the combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc) and gave the title compound as an yellow oil. 13C-NMR (DMSO-d6) δ 165.3, 150.4, 150.0, 149.8, 149.3, 137.8, 122.2, 120.5, 118.8, 117.9, 114.0, 71.8, 55.7, 48.3, 18.6.

後処理

  1. customat 50-60° C
  2. additionwas added
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted several times with EtOAc
  5. washthe combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc)

出典と根拠

ORDレコード
ord-4a54bf290030467893716d7e6663d365
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08034811B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート