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Formamide → (1S)-1-(1-{[2-cyano-4-(1,3-thiazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422545
ノート
印刷プレビュー

反応式

HRID 2422545 の反応式
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]([NH2:17])=O.[N+:18]([C:21]1[CH:58]=[CH:57][C:24]([C:25]([O:27][C@@:28]([C:35]2[N:36]=[N:37][N:38]([CH2:40][C:41]3[CH:50]=[C:49]4[C:44]([C:45]([C:53](=O)[CH2:54]Br)=[CH:46][C:47]([C:51]#[N:52])=[N:48]4)=[CH:43][CH:42]=3)[CH:39]=2)([C:31]([F:34])([F:33])[F:32])[CH2:29][CH3:30])=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>O1CCOCC1.C(OCC)(=O)C>[N+:18]([C:21]1[CH:58]=[CH:57][C:24]([C:25]([O:27][C@@:28]([C:35]2[N:36]=[N:37][N:38]([CH2:40][C:41]3[CH:50]=[C:49]4[C:44]([C:45]([C:53]5[N:17]=[CH:15][S:2][CH:54]=5)=[CH:46][C:47]([C:51]#[N:52])=[N:48]4)=[CH:43][CH:42]=3)[CH:39]=2)([C:31]([F:34])([F:33])[F:32])[CH2:29][CH3:30])=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]
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 3

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 86621977(S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

生成物 1

HCID 66790904(1S)-1-(1-{[2-cyano-4-(1,3-thiazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

試薬・触媒・溶媒 2

HCID 8857
Ethyl Acetate
溶媒
HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution of P4S10 (34 mg, 0.08 mmol) in dioxane (1 mL) at 0° C. was added formamide (57 mg, 1.26 mmol). The reaction mixture was warmed to room temperature for 1 h. A solution of 1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (see Example 52, Step 2) (160 mg, 0.25 mmol) in dioxane (1 mL) was then added and the mixture stirred at room temperature overnight. The reaction mixture was diluted in ethyl acetate, washed with water, brine and dried over MgSO4. The crude compound was purified on silica gel (eluting solvent: 5% acetone in dichloromethane) to give the desired product. 1H NMR (acetone-d6): δ 9.35 (s, 1H), 8.80 (d, 1H), 8.55 (s, 1H), 8.40 (m, 3H), 8.30 (d, 2H), 8.22 (s, 1H), 8.05 (s, 1H), 7.75 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 1.15 (t, 3H).

後処理

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customThe crude compound was purified on silica gel (eluting solvent: 5% acetone in dichloromethane)

出典と根拠

ORDレコード
ord-3671ed42f7e14ef1b3a2a7c94000399e
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960409B2

反応ノート

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