Ammonia → HCID 178514411, compound

HRID 1171048Notes

Reaction equation

HRID 1171048 reaction equation
[Cl:1][C:2]1[C:3]([CH2:20][C:21](OC2C=CC=CC=2)=[O:22])=[N+:4]([O-:19])[C:5]([NH:8][CH2:9][C:10]([F:18])([F:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1.Cl.Cl.[C:32]([NH:35][O:36][CH2:37][CH2:38][NH2:39])(=N)[NH2:33].CC[N:42](C(C)C)C(C)C.N>C(Cl)Cl.CO.CO>[Cl:1][C:2]1[C:3]([CH2:20][C:21]([NH:39][CH2:38][CH2:37][O:36][NH:35][CH:32]=[N:33][NH2:42])=[O:22])=[N+:4]([O-:19])[C:5]([NH:8][CH2:9][C:10]([F:17])([F:18])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 178478838HCID 178478838, compoundHCID 178520314HCID 178520314, compound

Product 1

HCID 178514411HCID 178514411, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-chloro-6-(2,2-difluoro-2-phenyl-ethylamino)-2-phenoxycarbonylmethyl-pyridine 1-oxide (41.2 mg, 98.4 μmol), as prepared in Example 2d, N-[2-(amidinoaminooxy)ethylamine dihydrochloride (32.9 mg, 172 μmol), as prepared in the previous step, MeOH (0.50 mL), and DIPEA (66 μL, 379 μmol) were stirred at 70° C. for 40 min. The homogeneous dark amber solution yielded a heavy white precipitate. Application of this crude reaction mixture to a silica flash column (95:5 DCM/MeOH with saturated NH3 as eluent) yielded the title compound as an off-white solid (6.5 mg, 15%). 1H-NMR (300 MHz, CD3OD) δ 7.58-7.42 (m, 5H), 7.35 (d, 1H), 6.83 (d, 1H), 4.06 (t, J=13.7 Hz, 2H), 4.08 (s, 2H), 3.79 (t, 2H), 3.41 (t, 2H). LC/MS (ESI): calcd mass 442.1. found 443.3 (MH)+.

Workup

  1. customThe homogeneous dark amber solution yielded a heavy white precipitate

Sources & evidence

ORD record
ord-ed8450c601d849ed973eed4bb26e6b2b
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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