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Ammonia → 4-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide

HRID 1854627
ノート
印刷プレビュー

反応式

HRID 1854627 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([C:20]4[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.N.[OH:29]O>CCO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]([C:20]4[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:29])=[CH:22][CH:21]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=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

5

反応物 3

HCID 222Ammonia2 回HCID 784Hydrogen Peroxide2 回HCID 533122454-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile

生成物 1

HCID 533122444-(5-(6-(4-Methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzonitrile (Example 51, 40 mg, 0.11 mmol) was suspended in EtOH (8 ml). Aqueous ammonia (28-30%, 4 ml) was added followed by H2O2 (35%, 1 ml). The reaction mixture was stirred at 40° C. for 2.5 days. Aqueous ammonia (2 ml) and H2O2 (0.250 ml) were added and the reaction mixture was stirred a further 24 hours at 40° C. The reaction was partitioned between H2O (30 ml) and EtOAc (70 ml). After separation, the aqueous phase was extracted again with EtOAc (70 ml). After evaporation, and purification of the crude product by dry flash chromatography over SiO2 eluting with EtOAc/MeOH (5%-10%)/NEt3 (0.5%), 4-(5-(6-(4-methylpyridin-2-ylamino)pyridin-2-yl)thiazol-2-yl)benzamide was obtained as a yellow solid (46 mg, 74%). 1H NMR (300 MHz, DMSO-d6) δ 9.72 (br s, 1H), 8.59 (br s, 1H), 8.20-7.98 (m, 6H), 7.95 (d, J=8.6 Hz, 1H), 7.78-7.70 (m, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.57-7.45 (m, 3H), 2.25 (s, 3H). (APCI+) m/z 388 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred a further 24 hours at 40° C
  2. customThe reaction was partitioned between H2O (30 ml) and EtOAc (70 ml)
  3. customAfter separation
  4. extractionthe aqueous phase was extracted again with EtOAc (70 ml)
  5. customAfter evaporation, and purification of the crude product
  6. dry with materialby dry flash chromatography over SiO2 eluting with EtOAc/MeOH (5%-10%)/NEt3 (0.5%)

出典と根拠

ORDレコード
ord-2218a6f3b4994d40afa1942ead821c10
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962665B2

反応ノート

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