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

HRID 1519135

반응식

HRID 1519135 반응식
[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]

참가 물질

8

반응물 2

HCID 86724056N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amineHCID 178418361HCID 178418361, 화합물

생성물 2

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

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-edc56fd371044f14806834a9e4386899
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073875B2

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