Diisopropylethylamine → HCID 66576022, compound

HRID 1775567Notes

Reaction equation

HRID 1775567 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:15][N:14]=[C:13]2[N:23]([CH2:32][C:33](O)=[O:34])[N:24]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:12]=12.Cl.[CH3:37][N:38]([CH3:47])[CH2:39][CH2:40][CH2:41][N:42]=[C:43]=NCC.OC1C=CC=C[N+]=1[O-]>C(Cl)Cl>[Cl:10][C:11]1[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:15][N:14]=[C:13]2[N:23]([CH2:32][C:33]([N:42]3[CH2:41][CH2:40][CH:39]([N:38]([CH3:47])[CH3:37])[CH2:43]3)=[O:34])[N:24]=[C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:12]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acidHCID 178526252HCID 178526252, compound

Product 1

HCID 66576022HCID 66576022, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diisopropylethylamine (DIPEA) (120 μL, 0.67 mmol) and N,N-dimethylpyrrolidine (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 then N,N-dimethylpyrrolidine (10 mg, 0.09 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 67 as a white solid (27.3 mg).

Workup

  1. customThe solution obtained
  2. customAfter a further 3.5 h the reaction was purified

Sources & evidence

ORD record
ord-7eff920f5a1e40639a26d6d202b53cdc
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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