HCID 178510254, compound → HCID 178510251, compound

HRID 1875135Notes

Reaction equation

HRID 1875135 reaction equation
[N:1]([C:4]1[NH:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[N:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Cl:9])[N:8]=1)=[N+]=[N-]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCOC(C)=O>[NH2:1][C:4]1[NH:5][C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[N:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Cl:9])[N:8]=1

Participants

4

Reactant 1

HCID 178510254HCID 178510254, compound

Product 1

HCID 178510251HCID 178510251, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in a similar manner to that described herein using 2-azido-4-chloro-N-({4-chloro-3-[(2-chloro-6-cyano-4-pyridinyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (123 mg, 0.255 mmol), a catalytic amount of Lindlar catalyst in EtOAc (15 ml) under H2 (50 psi) to afford the title compound as a white powder (52 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.96 (1H, s) 7.98 (1H, d) 7.78 (1H, t) 7.59 (1H, d) 7.53 (1H, d) 7.39 (1H, t) 5.83 (2H, s) 4.50 (2H, d). LCMS: m/z 455 (M+1).

Workup

  1. customThe title compound was prepared in a similar manner to that

Sources & evidence

ORD record
ord-a839e05f44bd4a999d068036df68bcd6
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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