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Ammonium Chloride → 3-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochloride

HRID 1426106
ノート
印刷プレビュー

反応式

HRID 1426106 の反応式
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][O:13][C:14]1[C:15]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-:49]>C1COCC1>[ClH:49].[CH3:26][C:24]1[N:25]=[C:21]([NH:20][C:15]2[C:14]([O:13][CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)[S:22][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 727058253-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

生成物 1

HCID 866396593-((2-(4-Methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochloride収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

A 125 mL round-bottomed flask was charged with 3-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (5.4 g, 13 mmol) and THF (50 mL). TBAF (1M in THF, 15 mL, 15 mmol) was added and stirred at room temperature overnight. The reaction was poured into saturated aqueous NH4Cl and extracted with CH2Cl2 (2×100 mL). The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified over silica gel (30 to 80% EtOAc in hexanes) to afford 3-((2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)methyl)phenol hydrochloride (3.5 g, 79%) after HCl salt formation. 1H NMR (d6-DMSO) δ 9.83 (bs, 1H), 9.50 (bs, 1 h), 7.89 (dd, 1H), 7.38 (d, 1H), 7.22 (t, 1H), 6.98 (m, 2H), 6.91 (dd, 1H), 6.75 (dd, 1H), 6.62 (s, 1H), 5.22 (s, 2H), 2.29 (s, 3H). Mass spectrum (apci) m/z=314.1 (M+H-HCl).

後処理

  1. extractionextracted with CH2Cl2 (2×100 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified over silica gel (30 to 80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-2e20642a36ed4274967f1da790f16cb2
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933077B2

反応ノート

読み込み中…

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