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Water → 4-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

HRID 578628
ノート
印刷プレビュー

反応式

HRID 578628 の反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1.C1N=C[N:28](C(N2C=NC=C2)=O)C=1.[NH4+].[Cl-].O>CS(C)=O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][C:8]1[C:17]2[C:12](=[C:13]([C:18]([NH2:28])=[O:19])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][N:9]=1
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

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 667637834-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acid

生成物 1

HCID 667623904-{[3-(Trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide収率 92%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-{[3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxylic acid (68 mg, 0.19 mmol) in 2 mL of anhydrous DMSO, CDI (47 mg, 0.29 mmol, 1.5 equiv.) was added. The resulting mixture was stirred at 50° C. for 3 h. After cooling down to rt, NH4Cl (22 mg, 0.29 mmol, 1.5 equiv.) was added. The reaction mixture was stirred at rt overnight. The reaction mixture was poured into water. The white precipitate was collected as the desired product by filtration, followed by washed with water in 92% yield. 1HNMR (In DMSO): 4.90 (d, J=5.9 Hz, 2H), 7.56-7.69 (m, 4H), 7.74 (s, 1H), 7.86 (d, J=3.7 Hz, 1H), 8.51 (dd, J=1.5 and 8.0 Hz, 1H), 8.58 (dd, J=1.5 and 7.7 Hz, 1H), 8.59 (s, 1H), 9.24 (t, J=5.9 Hz, 1H), 10.33 (d, J=3.7 Hz, 1H). Mass: M+H+: 347.

後処理

  1. temperatureAfter cooling down to rt
  2. stirringThe reaction mixture was stirred at rt overnight
  3. filtrationThe white precipitate was collected as the desired product by filtration
  4. washby washed with water in 92% yield

出典と根拠

ORDレコード
ord-08fdda18b1eb4494a41705b94017a1a6
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040560B2

反応ノート

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