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Ammonium Chloride → [(8-amino-3-{1-[(cyclopropylmethyl)amino]-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl)oxy]acetonitrile

HRID 601366
ノート
印刷プレビュー

反応式

HRID 601366 の反応式
[CH:1]1([CH2:4][NH:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([O:30][CH2:31][C:32]#[N:33])=[C:26]([N+:27]([O-])=O)[C:20]=4[S:19](=[O:35])(=[O:34])[N:18]=3)[C:7]2=[O:36])[CH2:3][CH2:2]1.[Cl-].[NH4+]>CO.O1CCCC1.O.[Fe]>[NH2:27][C:26]1[C:20]2[S:19](=[O:35])(=[O:34])[N:18]=[C:17]([C:8]3[C:7](=[O:36])[N:6]([NH:5][CH2:4][CH:1]4[CH2:3][CH2:2]4)[C:15]4[C:10]([C:9]=3[OH:16])=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:22][C:21]=2[CH:23]=[CH:24][C:25]=1[O:30][CH2:31][C:32]#[N:33]
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

5

反応物 2

HCID 25517Ammonium ChlorideHCID 136358422[(3-{1-[(cyclopropylmethyl)amino]-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl}-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl)oxy]acetonitrile

生成物 1

HCID 136358500[(8-amino-3-{1-[(cyclopropylmethyl)amino]-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl)oxy]acetonitrile収率 41.6%

試薬・触媒・溶媒 2

HCID 23925Iron触媒
HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
60 °C

実験手順

A mixture of the product of Example 388A (13 mg, 0.025 mmol), iron powder (6.0 mg, 0.107 mmol), and ammonium chloride (1.5 mg, 0.028 mmol) in methanol:tetrahydrofuran:water (2:2:1, 2 mL) was heated at 60° C. for 1 hour. The solution filtered through Celite® and washed with tetrahydrofuran. The solution was evaporated under reduced pressure and the residue was triturated with ethyl acetate, filtered washed with water and dried to give title compound (5 mg, 41%). 1H NMR (300 MHz, DMSO-d6) δ 0.14 (d, J=1.11 Hz, 2 H) 0.41 (d, J=5.88 Hz, 2 H) 1.01 (m, 1 H) 2.85 (d, J=5.40 Hz, 2 H) 5.23 (s, 2 H) 5.80 (s, 2 H) 6.45 (s, 1 H) 6.83 (d, J=8.46 Hz, 1 H) 7.38 (d, J=8.46 Hz, 1 H) 7.44 (t, J=7.02 Hz, 1 H) 7.90 (t, J=7.02 Hz, 1 H) 8.10 (d, J=8.46 Hz, 1 H) 8.16 (d, J=7.74 Hz, 1 H) 13.93 (s, 1 H) 14.94 (s, 1 H). MS (ESI−) m/z 479 (M−H)−.

後処理

  1. filtrationThe solution filtered through Celite®
  2. washwashed with tetrahydrofuran
  3. customThe solution was evaporated under reduced pressure
  4. customthe residue was triturated with ethyl acetate
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-812017c9ebfe4893bfd94d777353615e
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902203B2

反応ノート

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