Diisopropylethylamine → HCID 66576020, compound

HRID 1775565Notes

Reaction equation

HRID 1775565 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][N:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[Cl:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:23][N:22]=[C:21]2[N:31]([CH2:40][C:41](O)=[O:42])[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]=12.Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-]>C(Cl)Cl>[Cl:18][C:19]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:23][N:22]=[C:21]2[N:31]([CH2:40][C:41]([N:14]3[CH2:15][CH2:16][CH2:17][N:11]([CH3:10])[CH2:12][CH2:13]3)=[O:42])[N:32]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]=12

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acidHCID 178526252HCID 178526252, compound

Product 1

HCID 66576020HCID 66576020, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diisopropylethylamine (DIPEA) (120 μL, 0.67 mmol) and 1-methyl 1,4-diazepane (34 mg, 0.3 mmol) in CH2Cl2 (1 mL) was added to a mixture of 2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid (100 mg, 0.27 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (60 mg, 0.3 mmol) and 2-hydroxypyridine-N-oxide (HOPO) (30 mg, 0.27 mmol). The solution obtained was stirred at room temperature for 18 h. The reaction was purified using chromatography (silica gel, gradient 0 to 5% triethylamine/acetone) followed by preparative HPLC yielding Compound 65 as a white solid (25 mg).

Workup

  1. customThe solution obtained
  2. customThe reaction was purified

Sources & evidence

ORD record
ord-31186acd37884fc0aa27345c047e1fca
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

Loading…