Hydrogen Bromide → (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine

HRID 446911ノート

反応式

HRID 446911 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[S:13][C:12]3=[N:14][N:15]=[C:16]([C@H:17]([NH:19]C(=O)OCC4C=CC=CC=4)[CH3:18])[N:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br>C(O)(=O)C.O>[NH2:19][C@@H:17]([C:16]1[N:11]2[C:12]([S:13][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:10]2)=[N:14][N:15]=1)[CH3:18]

参加物

5

反応物 2

HCID 260Hydrogen BromideHCID 86642295(R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate

生成物 1

HCID 59363289(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine収率 70.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

(Step 8-iii) To a slurry of (R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate (0.39 g, 0.92 mmol) in acetic acid (20 mL) was added 48% hydrobromic acid in water (10 mL). The mixture was heated to 90° C. for 2 hours. After cooling to room temperature, the resulting solution was concentrated to ⅓ the original volume, poured on ice and the pH adjusted to 8 with 2N sodium hydroxide. The resulting precipitate was filtered, washed with water, and dried overnight in vacuo to provide (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine (0.19 g): ESMS MH+=294.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe resulting solution was concentrated
  3. additionpoured on ice
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried overnight in vacuo

出典と根拠

ORDレコード
ord-6446ea2ea20d4ac58d1082da7b13e87c
出典データセット
uspto-grants-2013_07
特許番号
US08481538B2

反応ノート

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