Methyl 2,2,2-trichloroacetimidate → HCID 86730074, compound

HRID 2272714Notes

Reaction equation

HRID 2272714 reaction equation
[Cl:1][C:2]([Cl:8])([Cl:7])[C:3](=N)OC.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:12][C:11]=1[F:24]>C(O)(=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[N:23]=[C:3]2[C:2]([Cl:8])([Cl:7])[Cl:1])=[CH:12][C:11]=1[F:24]

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 61466916N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine

Product 1

HCID 86730074HCID 86730074, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 2,2,2-trichloroethanimidoate (0.743 mL, 6.00 mmol) was added to a solution of N2-(4-chloro-3-fluorophenyl)pyridine-2,3-diamine (C12) (951 mg, 4.00 mmol) in acetic acid (4 mL), and the reaction mixture was stirred at room temperature for 5 hours. After concentration in vacuo, the residue was purified via chromatography on silica gel (Gradient: 5% to 100% ethyl acetate in heptane) to afford the product as a white solid. Yield: 1.04 g, 2.85 mmol, 71%. LCMS m/z 366.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.49 (dd, J=4.7, 1.5 Hz, 1H), 8.27 (dd, J=8.1, 1.5 Hz, 1H), 7.64 (ddd, J=8.5, 7.8, 0.3 Hz, 1H), 7.42 (dd, J=8.1, 4.7 Hz, 1H), 7.39 (ddd, J=8.8, 2.4, 0.2 Hz, 1H), 7.32 (ddd, J=8.5, 2.4, 1.3 Hz, 1H).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified via chromatography on silica gel (Gradient: 5% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-81388b5b2a5d4f70b2f6f1ce59a011cc
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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