N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amine → Hydrochloric Acid

HRID 1519135ノート

反応式

HRID 1519135 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[N:12](CC2C=CC=CC=2)[N:13]=[N:14][CH:15]=1.[H][H]>CO.CCOC(C)=O.[Pd].Br[Zn]Br>[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[CH:15]=[N:14][NH:13][N:12]=1.[ClH:9]

参加物

8

反応物 2

HCID 86724056N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amineHCID 178418361HCID 178418361、化合物

生成物 2

HCID 313Hydrochloric AcidHCID 75203051N-(2-(Aminomethyl)-4-chlorophenyl)-2H-1,2,3-triazol-4-amine

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amine 7b (439 mg, 1.40 mmol) in dry MeOH (18 mL) and EtOAc (18 mL) was treated with dibromozinc (126.0 mg, 0.56 mmol). The degassed mixture was then treated with 10% palladium on carbon (297.8 mg, 0.28 mmol) before affixing a hydrogen balloon. The mixture was stirred at room temperature for 2 h before filtering through celite and concentrating. The material was purified on an ISCO (0-100% MeOH in DCM) and the freebase was stirred in 4N HCl in dioxane for 30 min before evaporating to afford the title compound I-34 (mono hydrochloride salt) as a solid (291 mg, 80%). 1H NMR (500 MHz, DMSO-d6) δ 8.52 (1H, s) 8.47 (3H, m), 7.63 (1H, d), 7.53 (s, 1H), 7.48 (1H, d), 7.31 (1H, d) 4.12 (2H, q). MS m/z: 224.1 (M+H)+.

後処理

  1. filtrationbefore filtering through celite
  2. concentrationconcentrating
  3. customThe material was purified on an ISCO (0-100% MeOH in DCM)
  4. stirringthe freebase was stirred in 4N HCl in dioxane for 30 min
  5. custombefore evaporating

出典と根拠

ORDレコード
ord-edc56fd371044f14806834a9e4386899
出典データセット
uspto-grants-2015_07
特許番号
US09073875B2

反応ノート

読み込み中…