4-Phenylbenzylamine → 3-[(Biphenyl-4-ylmethyl)amino]pyridine-4-carboxylic acid

HRID 1847148Notes

Reaction equation

HRID 1847148 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([CH2:11][NH:12][C:21]2[CH:22]=[N:23][CH:24]=[CH:16][C:17]=2[C:18]([OH:20])=[O:19])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 3449894-PhenylbenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 717667273-[(Biphenyl-4-ylmethyl)amino]pyridine-4-carboxylic acidYield 36%

Procedure

The title compound was prepared in 36% yield from 4-phenylbenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.55 (br s, 1H), 8.17 (s, 1H), 7.83 (d, 1H, J=5.0 Hz), 7.71 (m, 4H), 7.58 (d, 1H, J=5.0 Hz), 7.32-7.48 (m, 5H), 4.62 (s, 2H). [M+H] calc'd for C19H16N2O2, 305. Found 305.

Sources & evidence

ORD record
ord-9031a5d0c0d042c9bb362557a0b8e17d
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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