4-Methoxybenzylamine → HCID 59626688, compound

HRID 2400373Notes

Reaction equation

HRID 2400373 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:19]([CH2:28]Cl)=[C:20]2[C:24](=[C:25]([Cl:27])[CH:26]=1)[NH:23][N:22]=[CH:21]2)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:19]([CH2:28][NH:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)=[C:20]2[C:24](=[C:25]([Cl:27])[CH:26]=1)[NH:23][N:22]=[CH:21]2)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 516892Sodium BicarbonateHCID 66686043HCID 66686043, compound

Product 1

HCID 59626688HCID 59626688, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-{[(benzyloxy)carbonyl]amino}-3-(7-chloro-4-{chloromethyl}-1H-indazol-5-yl)propanoate (4.3 g, 9.17 mmol) in acetonitrile (100 mL) was added 4-methoxybenzyl amine (2.4 mL, 2.52 g, 18.34 mmol) and the solution stirred at room temperature for several hours. The reaction was poured into a saturated aqueous solution of sodium bicarbonate (500 mL) and the mixture extracted with ethyl acetate. The combined organic extracts were washed once with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure to give 4.1 g of the title compound. MS: m/z=537 (M+1).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic extracts were washed once with brine (100 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-206c07b566984887b9dd70ec92d6cee2
Source dataset
uspto-grants-2014_08
Patent number
US08796260B2

Reaction notes

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