Picolinic acid → HCID 64792821, compound

HRID 2308298Notes

Reaction equation

HRID 2308298 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](O)=[O:17].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CCN=C=NCCCN(C)C>>[OH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)=[O:17])=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 1018Picolinic acidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 693314-Aminobenzyl alcoholHCID 757711-Hydroxybenzotriazole

Product 1

HCID 64792821HCID 64792821, compoundYield 92%

Procedure

Using General Procedure F: Reaction of (4-Amino-phenyl)-methanol (200 mg, 1.63 mmol), picolinic acid (217 mg, 1.79 mmol), 1-hydroxybenzotriazole (242 mg, 1.79 mmol), 4-methyl morpholine (269 μL, 2.45 mmol) and EDCI (343 mg, 1.79 mmol) for 24 h at room temperature, gave the title compound (342 mg, 92%) as a red solid. 1H NMR (300 MHz, CDCl3) δ 4.70 (d, 2H, J=3.9 Hz), 7.41 (d, 2H, J=8.4 Hz), 7.50 (ddd, 1H, J=7.5, 4.8, 1.3 Hz), 7.79 (d, 2H, J=8.4 Hz), 7.92 (ddd, 1H, J=7.5, 7.5, 4.5 Hz), 8.31 (d, 1H, J=6.0 Hz), 10.06 (br s, 1H).

Sources & evidence

ORD record
ord-8186a1e5c63d4a3ebb3a92d9063a0a26
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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