1,2-Dichloroethane → HCID 178509941, compound

HRID 1875136Notes

Reaction equation

HRID 1875136 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:15][CH2:16][C:17]1[C:18]([F:34])=[C:19]([O:24][C:25]2[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=2)[C:28]#[N:29])[C:20]([Cl:23])=[CH:21][CH:22]=1.[NH:35]1[CH:39]=[N:38][C:37]([C:40](O)=[O:41])=[N:36]1>CN(C=O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:40]([C:37]2[N:38]=[CH:39][NH:35][N:36]=2)=[O:41])=[C:18]([F:34])[C:19]=1[O:24][C:25]1[CH:26]=[C:27]([C:28]#[N:29])[CH:30]=[C:31]([Cl:33])[CH:32]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 178524907HCID 178524907, compound

Product 1

HCID 178509941HCID 178509941, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a similar manner to that described herein using EDC (0.068 g, 0.354 mmol), HOBT (0.048 g, 0.354 mmol), 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.100 g, 0.321 mmol) and 1H-1,2,4-triazole-3-carboxylic acid (0.036 g, 0.321 mmol) in DMF (2 mL) to give title compound (0.051 g, 39%) as a white solid. 1H NMR (400 MHz, DMSO-d6) (95° C.) δ ppm 14.24 (br. s., 1H), 8.60 (br. s., 1H), 7.72 (s, 1H), 7.33-7.49 (m, 5H), 4.55 (d, 2H). ES MS: m/z 406 (M+1).

Workup

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

Sources & evidence

ORD record
ord-138676578efb4b6f99e7a9c33dc1b5fe
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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