N1,4,5-Trimethylbenzene-1,2-diamine → HCID 136492482, compound

HRID 508964Notes

Reaction equation

HRID 508964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=O)=[C:17]([O:25][CH3:26])[CH:16]=2)[N:10]=1.[CH3:27][NH:28][C:29]1[C:30]([NH2:37])=[CH:31][C:32]([CH3:36])=[C:33]([CH3:35])[CH:34]=1.C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]3[N:28]([CH3:27])[C:29]4[CH:34]=[C:33]([CH3:35])[C:32]([CH3:36])=[CH:31][C:30]=4[N:37]=3)=[C:17]([O:25][CH3:26])[CH:16]=2)[N:10]=1

Participants

5

Reactant 3

HCID 591611N1,4,5-Trimethylbenzene-1,2-diamineHCID 16682925TrimethylaluminumHCID 136492448methyl 4-(3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxybenzoate

Product 1

HCID 136492482HCID 136492482, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-31 by using methyl 4-(3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methoxybenzoate (step-2 of Intermediate-15, 0.100 g, 0.26 mmol), N1,4,5-trimethylbenzene-1,2-diamine (Intermediate-31, 0.048 g, 0.32 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) to afford 0.030 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.33 (s, 3H), 2.36 (s, 3H), 3.56 (s, 3H), 3.85 (s, 3H), 7.33 (s, 1H), 7.41 (s, 1H), 7.47-7.59 (m, 3H), 7.66-7.78 (m, 3H), 12.5 (br s, 1H); MS (m/z): 478.29 (M+H+).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6162db128f4d4b7db7eb3fec9394caad
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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