2-Fluorobenzylamine → HCID 21074212, compound

HRID 1373189Notes

Reaction equation

HRID 1373189 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([C:23](O)=O)[CH:22]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)=[O:9])([CH3:3])[CH3:2].[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30].C([BH3-])#N.[Na+]>CO>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:20]=[C:21]([CH2:23][NH:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[F:26])[CH:22]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)=[O:9])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 666492-FluorobenzylamineHCID 5003444Sodium cyanoborohydrideHCID 86594826HCID 86594826, compound

Product 1

HCID 21074212HCID 21074212, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-isopropyloxy-5-carboxy-benzoyl) amino-5-pyridine carboxylic acid (0.10 g, 0.30 mM), 4A molecular sieves (0.3 g) and 2-fluorobenzylamine were stirred in MeOH at ambient temperature for 2 hrs then sodium cyanoborohydride (0.023 g, 0.36 mM) added. After a further 2 hrs the reaction mixture was filtered, residue washed with MeOH and the filtrate concentrated in vacuo. Water was added, then acidified with 2M HCl to precipitate a colourless solid which was filtered, washed with water and dried under high-vacuum to give the title compound as a light brown solid (00.10 g, 76%); 1H NMR δ (d6-DMSO): 1H NMR δ (d6-DMSO): 1.29 (d, 6H), 4.13 (d, 2H), 4.74 (m, 1H), 7.20–7.30 (m, 3H), 7.43 (m, 1H), 7.58 (m, 2H), 7.68 (s, 1H), 8.28 (s, 2H), 8.87 (s, 1H), 11.10 (bs, 1H).

Workup

  1. filtrationAfter a further 2 hrs the reaction mixture was filtered
  2. washresidue washed with MeOH
  3. concentrationthe filtrate concentrated in vacuo
  4. additionWater was added
  5. customto precipitate a colourless solid which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under high-vacuum

Sources & evidence

ORD record
ord-dcd142fd6e144922a567d3ef9538575a
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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