Diisopropylethylamine → 4-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)-1-methylpiperazin-2-one

HRID 1775587Notes

Reaction equation

HRID 1775587 reaction equation
ClC1C(C2C=CC=CC=2)=NN=C2N(CCI)N=C(C3C=CC=CC=3)C=12.[Cl:26][C:27]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:31][N:30]=[C:29]2[N:39]([CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]3)[N:40]=[C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:28]=12.Cl.N1CCNCC1=[O:64].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:26][C:27]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:31][N:30]=[C:29]2[N:39]([CH2:48][CH2:49][N:50]3[CH2:51][CH2:52][N:53]([CH3:56])[C:54](=[O:64])[CH2:55]3)[N:40]=[C:41]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:28]=12

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 19094617Piperazin-2-one hydrochloride2×HCID 665762534-chloro-1-(2-(4-methylpiperazin-1-yl)ethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazineHCID 866970204-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine

Product 1

HCID 665762564-(2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethyl)-1-methylpiperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-1-(2-iodoethyl)-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (example 74 step 1 (Compound 81)) (100 mg, 0.21 mmol) in CH2Cl2 (1 ml) was added to piperazinone hydrochloride (160 mg, 1.05 mmol) and diisopropylethylamine (DIPEA) (220 μl, 12.6 mmol) in CH2Cl2 (0.5 ml) and the reaction stirred at ambient for 2 days. Further piperazinone hydrochloride (160 mg, 1.05 mmol) and diisopropylethylamine (DIPEA) (220 μl, 12.6 mmol) were added and the reaction stirred for a further 24 h. The resultant residue was purified using chromatography (silica gel, gradient 20 to 100% ethyl acetate/isohexane, then 0 to 100% ethyl acetate/acetone) followed by preparative HPLC to give Compound 84 as a yellow glass solid (17 mg).

Workup

  1. stirringthe reaction stirred for a further 24 h
  2. customThe resultant residue was purified

Sources & evidence

ORD record
ord-9a68fd568b8d4233928074ae794acde6
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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