Pyridine → HCID 68874909, compound

HRID 490183

Reaction equation

HRID 490183 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[C:8]([CH3:10])[C:6]([NH2:7])=[C:5]([CH3:11])[CH:4]=1.Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=1.[C:25](=[O:28])([O-])[O-].[Na+].[Na+].N1C=CC=C[CH:32]=1>>[Cl:2][C:3]1[CH:9]=[C:8]([CH3:10])[C:6]([NH:7][C:25](=[O:28])[CH2:32][N:22]2[CH2:21][CH:20]=[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)[CH2:24][CH2:23]2)=[C:5]([CH3:11])[CH:4]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 184069814-Chloro-2,6-dimethylaniline--hydrogen chloride (1/1)HCID 688728301',2',3',6'-Tetrahydro-2,4'-bipyridine hydrochloride

Product 1

HCID 68874909HCID 68874909, compound

Procedure

The title compound was prepared according to the method of Example 170 substituting 4-chloro-2,6-dimethylaniline hydrochloride in place of 2,6-diethylaniline; substituting 1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl hydrochloride (Saari, W. S.; et al. J. Med. Chem. 1984, 27, 1182) in place of the product from Example 36C; and, adding one additional equivalent each of pyridine and sodium carbonate. The purification also employed 0.1% aqueous trifluoroacetic acid in place of aqueous ammonium acetate (10 mM). (yield: 53 mg, 0.075 mmol, 29%). 1H NMR (300 MHz, DMSO-d6) δ 2.18 (s, 6H), 2.92 (m, 2H), 3.46 (m, 1H), 3.68 (m, 1H), 4.03 (m, 1H), 4.14 (m, 1H), 4.38 (s, 2H), 6.73 (br s, 1H), 7.23 (s, 2H), 7.34 (m, 1H), 7.66 (br d, J=8.4 Hz, 1H), 7.85 (ddd, J=2.1, 7.5, 7.5 Hz, 1H), 8.59 (m, 1H), 10.0 (s, 1H); MS (ESI) m/e 356 (M+H)+; Anal. calcd for C20H22ClN3O.3.1 C2HF3O2: C, 44.36; H, 3.57; N, 5.92. Found: C, 44.31; H, 3.60; N, 5.91.

Workup

  1. customThe purification also employed 0.1% aqueous trifluoroacetic acid in place of aqueous ammonium acetate (10 mM)

Sources & evidence

ORD record
ord-c0e5473100b44c28b958588006d5417a
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Linked notes

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