Pyridine → HCID 19001394, compound

HRID 2259613Notes

Reaction equation

ClC(O[C:6](=[O:12])OC(Cl)(Cl)Cl)(Cl)Cl.N1C=CC=CC=1.Cl.[F:20][C:21]([F:40])([F:39])[C:22]1[CH:27]=[CH:26][C:25]2[C:28]3[C:32]([C:35]([O:37][CH3:38])=[O:36])([CH2:33][O:34][C:24]=2[CH:23]=1)[CH2:31][NH:30][N:29]=3.[NH2:41][C:42]1[CH:43]=[CH:44][C:45]([Cl:48])=[N:46][CH:47]=1>C(O)C.C(Cl)Cl>[Cl:48][C:45]1[N:46]=[CH:47][C:42]([NH:41][C:6]([N:30]2[CH2:31][C:32]3([C:35]([O:37][CH3:38])=[O:36])[CH2:33][O:34][C:24]4[CH:23]=[C:22]([C:21]([F:39])([F:20])[F:40])[CH:27]=[CH:26][C:25]=4[C:28]3=[N:29]2)=[O:12])=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.15 g (0.0005 mol) of bis(trichloromethyl)carbonate, 20 mL of methylene chloride and 0.39 mL (0.0048 mol) of pyridine was added 0.5 g (0.0015 mol) of the product from Step H at 0° C. The resulting mixture was stirred at 0° C. for 2 hours and then 0.21 g (0.0016 mol) of 5-amino-2-chloro pyridine was added. The resulting mixture was stirred at room temperature for 12 hours and then 10 mL of ethanol followed by 3 g of silica gel were added and the solvent was removed. Flash chromatography of the residue on silica gel using 2:1 hexanes-EtOAc gave 0.28 g of an off-white solid that melted at 236°-238° C. 1H NMR (CDCl3, 200 MHz) δ3.77 (s, 3H), 3.85 (d, 1H), 4.24 (d, 1H), 4.53 (d, 1H), 5.07 (d, 1H), 7.20-7.35 (m, 3H), 7.98 (d, 1H), 8.02 (s, 1H), 8.12 (dd, 1H), 8.42 (d, 1H).

Workup

stirringThe resulting mixture was stirred at room temperature for 12 hours
additionwere added
customthe solvent was removed

Sources & evidence

ORD record: ord-9534aac3c4344aecb19a70df57b7adea
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05474998

Reaction notes

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