1,1,1-Trimethoxy-2-chloroethane → 3-(chloromethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

HRID 446902

反応式

HRID 446902 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:10]=[N:11][C:12]([NH:15][NH2:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:17][CH2:18][C:19](OC)(OC)OC>Cl.CCOCC>[Cl:17][CH2:18][C:19]1[N:11]2[N:10]=[C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH:14]=[CH:13][C:12]2=[N:15][N:16]=1

参加物

4

反応物 2

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 59363292N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine

生成物 1

HCID 593632983-(chloromethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine収率 80%

試薬・触媒・溶媒 1

HCID 10953452Ether hydrochloride溶媒

実験手順

(Step 3-i) N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine (4.0 g, 17 mmol)) was taken up in HCl/Et2O (20 mL) and stirred for 10 min. The reaction mixture was concentrated, taken up in DMF (20 mL), and 2-chloro-1,1,1-trimethoxyethane (5.2 g, 34 mmol) was added. After stirring for 3 hours, a precipitate began to form. After one hour additional stirring, the reaction mixture was filtered to give the product, 3-(chloromethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine, as a white solid. (4 g, 13.6 mmol, 80% yield): 1H-NMR (500 MHz, DMSO-d6) 10.40 (s, 1H), 8.19 (d, J=9.8 Hz, 1H), 8.13 (t, J=1.8 Hz, 1H), 7.68 (dd, J=1.7, 8.2 Hz, 1H), 7.40 (t, J=8.1 Hz, 1H), 7.28 (d, J=9.9 Hz, 1H), 7.11-7.09 (m, 1H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. stirringAfter stirring for 3 hours
  3. customto form
  4. waitAfter one hour additional stirring
  5. filtrationthe reaction mixture was filtered

出典と根拠

ORDレコード
ord-56d28f58201b48f5bb87d22cab4b975b
出典データセット
uspto-grants-2013_07
特許番号
US08481538B2

関連ノート

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