Pivaloyl chloride → HCID 136246038, compound

HRID 59543Notes

Reaction equation

HRID 59543 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:25])=[C:7]([C:9]2[NH:10][C:11](=[O:24])[N:12]([C:14]3[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[N:13]=2)[CH:8]=1.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].CCN(C(C)C)C(C)C>C1COCC1>[Cl:25][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:8][C:7]=1[C:9]1[NH:10][C:11](=[O:24])[N:12]([C:14]2[CH:15]=[N:16][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:18][CH:19]=2)[N:13]=1

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 1364924525-(5-(aminomethyl)-2-chlorophenyl)-2-(6-(trifluoromethyl) pyridin-3-yl)-2H-1,2,4-triazol-3(4H)-one

Product 1

HCID 136246038HCID 136246038, compoundYield 18.7%

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-(6-(trifluoromethyl)pyridin-3-yl)-2H-1,2,4-triazol-3(4H)-one (Intermediate-91, 0.350 g, 0.945 mmol), pivaloyl chloride (0120 g, 0.945 mmol), DIPEA (2.0 mL), dry THF (10 mL) to afford 0.080 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.11 (s, 9H), 4.30 (d, J=6.3 Hz, 2H), 7.43 (d, J=8.4 Hz, 1H), 7.61-7.64 (m, 2H), 8.06 (d, J=9.0 Hz, 1H), 8.19 (m, 1H), 8.58 (d, J=8.4 Hz, 1H), 9.32 (s, 1H), 12.82 (s, 1H); MS (m/z): 454.50 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a8df358b2c4d47c1b58ef7b175085911
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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