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Acetic Acid → (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-methyl-amine

HRID 1170521
ノート
印刷プレビュー

反応式

HRID 1170521 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH:16]3[C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]4[CH:31]=[CH:30][N:29]=[CH:28]4)[N:21]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C=O.[C:34](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH:16]3[C:20]3[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]4[CH:31]=[CH:30][N:29]=[CH:28]4)[N:21]=3)[CH3:34])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59551907(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-amine

生成物 1

HCID 11633463(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-methyl-amine
収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-amine (65 mg, 156 μmol), formalin (63 μL, 780 μmol), and acetic acid (170 μL, 2.83 mmol) in MeOH (1 mL) was stirred at r.t. for 5 min. Sodium triacetoxyborohydride (99 mg, 470 μmol) was then added. The reaction mixture was stirred at r.t. for 20 min and then concentrated to residue. EtOAc (5 mL) and 1N NaOH (5 mL) were added. The organic layer was isolated, dried (MgSO4), filtered, and concentrated. Silica gel chromatography (0% to 10% MeOH/DCM) afforded 60 mg (89%) of (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-methyl-amine. [M+H]+ 435.32; 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 7.88 (s, 1H), 7.33 (s, 1H), 7.12 (s, 1H), 6.65-6.79 (m, 3H), 4.21 (s, 4H), 3.54 (t, 1H), 3.24-3.42 (m, 3H), 2.76 (m, 1H), 2.11-2.55 (m, 8H), 2.15 (s, 3H), 1.84 (m, 2H), 1.70 (m, 1H).

後処理

  1. concentrationconcentrated to residue
  2. additionEtOAc (5 mL) and 1N NaOH (5 mL) were added
  3. customThe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-89b806eebdf44bcaa40320dadd9333a1
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07825256B2

反応ノート

読み込み中…

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