2-Chloronicotinic acid → HCID 59599546, compound

HRID 2267033Notes

Reaction equation

HRID 2267033 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[CH:13]=[C:14]([CH:30]=[CH:31][CH:32]=1)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[C:19]([OH:26])[C:18]=1[CH2:27][CH2:28][CH3:29]>>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:14]2[CH:13]=[C:12]([NH:11][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])[CH:32]=[CH:31][CH:30]=2)=[C:18]([CH2:27][CH2:28][CH3:29])[C:19]=1[OH:26])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 762582-Chloronicotinic acidHCID 145235601-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one

Product 1

HCID 59599546HCID 59599546, compoundYield 9.1%

Procedure

Heat a mixture of 2-chloro-nicotinic acid (132 mg, 0.835 mmol) and 1-[4-(3-amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (250 mg, 0.835 mmol) to 130° C. After 18 hours, cool to ambient temperature and purify via flash chromatography (ethyl acetate:hexanes) to give a residue which was further purified by reverse phase chromatography (methanol:acetic acid:water) to yield the title product as a yellow solid (32 mg, 9%): 1H NMR (DMSO-d6) δ 0.88 (t, 3H), 1.51 (sextet, 2H), 2.57 (s, 3H), 2.63 (t, 2H), 5.27 (s, 2H), 6.73 (d, 1H), 6.87 (dd, 1H), 7.06 (d, 1H), 7.34 (t, 1H), 7.67 (d, 1H), 7.81 (d, 1H), 7.88 (s, 1H), 8.26 (dd, 1H), 8.36 (dd, 1H), 10.66 (bs, 1H), 12.85 (s, 1H), 13.63 (bs, 1H); MS (esi negative) m/z (rel intensity) 419 (100).

Workup

  1. temperatureHeat
  2. custompurify via flash chromatography (ethyl acetate:hexanes)
  3. customto give a residue which
  4. customwas further purified by reverse phase chromatography (methanol:acetic acid:water)

Sources & evidence

ORD record
ord-ae530ed56ca64a85bc9456bc087a0a51
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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