Cyclopropylamine → N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

HRID 857802Notes

Reaction equation

HRID 857802 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH:18]=[N:17][N:16]=[N:15]1)=[O:4].[CH:19]1([NH2:22])[CH2:21][CH2:20]1>C(Cl)Cl>[Cl:13][C:11]1[CH:10]=[CH:9][C:8]([N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[C:7]([CH:12]=1)[CH2:6][NH:5][C:3](=[O:4])[CH2:2][NH:22][CH:19]1[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 21866240HCID 21866240, compound

Product 1

HCID 69656285N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]acetamide (206 mg, 0.62 mmol) in CH2Cl2 (2.5 mL) at room temperature was added cyclopropylamine (500 μL, 7.22 mmol). The resulting yellow solution was stirred under N2 atmosphere for 1 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (gradient elution with EtOAc then with 10% MeOH-EtOAc) to afford the title compound as a yellow solid after drying in vacuo. 1H NMR (400 MHz, CDCl3): δ 8.97 (s, 1 H), 7.62–7.58 (m, 2 H), 7.46 (dd, J=1.8, 8.6 Hz, 1 H), 7.29–7.27 (m, 1 H), 4.24 (d, J=6.4 Hz, 2 H), 3.37 (s, 2 H), 2.23–2.18 (m, 1 H), 1.63 (br m, 1 H), 0.49–0.40 (m, 2 H), 0.37–0.36 (m, 2 H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (
  3. washgradient elution with EtOAc

Sources & evidence

ORD record
ord-26a1eb452de04450ab713aa894257c2a
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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