Diisopropylethylamine → HCID 66576021, compound
Reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)(=[O:12])[CH3:11].[Cl:19][C:20]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:24][N:23]=[C:22]2[N:32]([CH2:41][C:42](O)=[O:43])[N:33]=[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:21]=12.Cl.CN(C)CCCN=C=NCC.OC1C=CC=C[N+]=1[O-]>C(Cl)Cl>[C:10]([N:13]1[CH2:18][CH2:17][N:16]([C:42](=[O:43])[CH2:41][N:32]2[C:22]3=[N:23][N:24]=[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]([Cl:19])=[C:21]3[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[N:33]2)[CH2:15][CH2:14]1)(=[O:12])[CH3:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of diisopropylethylamine (DIPEA) (120 μL, 0.67 mmol) and 1-acetylpiperazine (38 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 then 1-acetylpiperazine (10 mg, 0.08 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (30 mg, 0.15 mmol) were added. After a further 3.5 h the reaction was purified using chromatography (silica gel, gradient 0 to 5% triethylamine/acetone) followed by preparative HPLC yielding Compound 66 as a white solid (32.2 mg).
Workup
- customThe solution obtained
- customAfter a further 3.5 h the reaction was purified
Sources & evidence
- ORD record
- ord-dfe6631eed484ff096b54ebc4a0ea2a2
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260381B2
Reaction notes
Loading…