Pivaloyl chloride → N-(3-(1-tert-Butyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)pivalamide

HRID 59527Notes

Reaction equation

HRID 59527 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[NH:8][C:7]([C:11]2[CH:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][C:12]=2[Cl:19])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>C1COCC1>[C:1]([N:5]1[C:9](=[O:10])[NH:8][C:7]([C:11]2[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=2[Cl:19])[CH2:17][NH:18][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 1366125162-tert-Butyl-5-(5-(aminomethyl)-2-chlorophenyl)-2H-1,2,4-triazol-3(4H)-one

Product 1

HCID 136612559N-(3-(1-tert-Butyl-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-4-chlorobenzyl)pivalamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in Example-108 by using 2-tert-butyl-5-(5-(aminomethyl)-2-chlorophenyl)-2H-1,2,4-triazol-3(4H)-one (Intermediate-75, 0.250 g), pivaloyl chloride (1.0 mL), DIPEA (2.0 mL), and dry THF (5 mL) to afford 0.180 g of desired product. 1H NMR (400 MHz, DMSO d6): δ 1.08 (s, 9H), 1.49 (s, 9H), 4.24 (d, J=4.5 Hz, 2H), 7.32 (dd, J=4.5 Hz, 3.6 Hz, 2H), 7.43 (s, 1H), 7.50 (s, 1H), 8.14 (d, J=4.5 Hz, 1H); MS (m/z): 365.20 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e11d70f7bab14f62927872ab8a081c4a
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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