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Acetic Acid → 3-Benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1795985
ノート
印刷プレビュー

反応式

HRID 1795985 の反応式
C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:19][CH:20]([C:23]1[N:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27](=[O:36])[C:26]2=[CH:37][CH:38]=[CH:39][N:25]2[N:24]=1)[CH2:21][CH3:22].[C:40]1(=O)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>ClCCCl>[CH2:29]([N:28]1[C:27](=[O:36])[C:26]2=[CH:37][CH:38]=[CH:39][N:25]2[N:24]=[C:23]1[CH:20]([NH:19][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[CH2:21][CH3:22])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 221799762-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

生成物 1

HCID 221800673-Benzyl-2-(1-cyclohexylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one収率 91%

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒

実験手順

Acetic acid (65 μl, 0.95 mmol) and sodium triacetoxyborohydride (200 mg, 0.95 mmol) were added to a solution of 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 180 mg, 0.64 mmol) and cyclohexanone (62 mg, 0.64 mmol) in 1,2-dichloroethane (5 mL). The mixture was stirred for 4 h at room temperature concentrated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was separated, dried (MgSO4) and concentrated to give the title compound (211 mg, 91%) as a white solid: 1H NMR (DMSO-d6) δ 0.69–1.19 (m, 10H), 1.38–1.89 (m, 6H), 1.99 (m, 1H), 3.63 (m, 1H), 4.82 (m, 1H), 5.80 (m, 1H), 6.55 (s, 1H), 7.06 (s, 1), 7.15 (m, 2H), 7.22–7.35 (m, 4H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ee96c8deb2e541ba8c7d76addf282a91
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07030118B2

反応ノート

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