Pivaloyl chloride → N-(4-chloro-3-(1-(4-(2-cyclopropylethynyl)-2-fluorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)pivalamide

HRID 59563Notes

Reaction equation

HRID 59563 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:27])=[C:7]([C:9]2[NH:10][C:11](=[O:26])[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH:22]4[CH2:24][CH2:23]4)=[CH:16][C:15]=3[F:25])[N:13]=2)[CH:8]=1.[C:28](Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[Cl:27][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][C:7]=1[C:9]1[NH:10][C:11](=[O:26])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][CH:22]3[CH2:24][CH2:23]3)=[CH:16][C:15]=2[F:25])[N:13]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 136492513HCID 136492513, compound

Product 1

HCID 136245921N-(4-chloro-3-(1-(4-(2-cyclopropylethynyl)-2-fluorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)benzyl)pivalamideYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in Example-108 by using 5-(5-(aminomethyl)-2-chlorophenyl)-2-(4-(2-cyclopropylethynyl)-2-fluorophenyl)-2H-1,2,4-triazol-3(4H)-one (0.100 g, 0.266 mmol), pivaloyl chloride (0.040 g, 0.319 mmol), THF (10.0 mL) and TEA (2 mL) to afford 0.040 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 0.78 (m, 2H), 0.919 (m, 2H), 1.11 (br s, 9H), 1.56 (m, 1H), 4.28 (br d, 2H), 7.32-7.41 (m, 3H), 7.56 (br s, 3H), 8.16 (s, 1H), 12.46 (s, 1H); MS (m/z): 467.22 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-9cc378fbc749463b8c809f45604a85a5
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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