3-Pyridinecarboxaldehyde → 4-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid salt

HRID 2121169Notes

Reaction equation

HRID 2121169 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.Cl.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:12]=1.[BH3-]C#N.[Na+]>C(O)(=O)C.CO>[C:15]([OH:17])(=[O:16])[CH3:14].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:12]=2)[CH:2]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 698924925-Amino-[1,1'-biphenyl]-2-carboxylic acid hydrochloride

Product 1

HCID 698936704-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid saltYield 186.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

3-Pyridinecarboxaldehyde (1.2 mL, 12.8 mmol) and 4-amino-2-phenylbenzoic acid hydrochloride (3.2 g, 12.8 mmol), prepared in Example 190A, were dissolved in 100 mL 1% acetic acid in methanol. After stirring for 10 minutes, NaBH3CN was added, and stirring was continued for 18 hours. The reaction was evaporated to dryness under reduced pressure and partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The organic extracts were combined, washed with brine, and dried over Na2SO4 to give 4-(3-Pyridylmethylamino)-2-phenylbenzoic acid acetic acid salt (4.35 g, 90%) of the title compound. MS m/e 305 (M+H)+. 1H NMR (d6-DMSO, 300 MHz) δ 4.41 (s, 2H), 6.45 (d, J=3 Hz, 1H), 6.60 (m, 1H), 7.15-7.90 (m, 10H), 8.48 (m, 1H), 8.60 (m, 1H).

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. customThe reaction was evaporated to dryness under reduced pressure
  4. custompartitioned between ethyl acetate and water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-649e3c7f17444ebf92ab17b16b1a94a7
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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