Triethylamine → HCID 86597211, compound

HRID 2424455Notes

Reaction equation

HRID 2424455 reaction equation
[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7].[O:21]1[C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=[N:22]1.C(N(CC)CC)C>ClCCl>[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:26]([C:25]3[O:21][N:22]=[CH:23][CH:24]=3)=[O:27])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2736707Isoxazole-5-carbonyl chlorideHCID 668493226-Piperazin-1-yl-pyridazin-3-carboxylic acid (3-methylbutyl)amide

Product 1

HCID 86597211HCID 86597211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide (277 mg, 1 mmol) in dichloromethane (15 mL) was added isoxazole-5-carbonyl chloride (1.0 mmol) as a dichloromethane solution in the presence of triethylamine (0.4 mL) at ambient temperature. After 1 hour the mixture was evaporated and the residue was subjected to column chromatography. Final product was isolated as a solid (0.107 g, yield 29%). 1H NMR (300 MHz, CDCl3) δ 8.34, 8.05, 7.83, 7.00, 6.86, 3.90-3.84, 3.51-3.45, 1.75-1.62, 1.53-1.46, 0.92. MS (ES+) m/z 373.3 (M+1).

Workup

  1. customAfter 1 hour the mixture was evaporated

Sources & evidence

ORD record
ord-7c95a85a5b31494d933de27a4ad4d6a9
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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