Dimethylpiperazine → HCID 136186311, compound

HRID 1467725Notes

Reaction equation

HRID 1467725 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3=[N:14][NH:15][C:16](=[O:21])[C:17]4[CH:18]=[CH:19][CH:20]=[C:11]([C:12]=43)[NH:10][CH:9]2[C:22]2[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH:32]1[CH3:37]>C(Cl)Cl>[CH3:37][CH:32]1[N:31]([CH3:30])[CH2:36][CH2:35][N:34]([CH2:26][C:25]2[CH:24]=[CH:23][C:22]([CH:9]3[NH:10][C:11]4[C:12]5[C:13](=[N:14][NH:15][C:16](=[O:21])[C:17]=5[CH:18]=[CH:19][CH:20]=4)[CH:8]3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:29][CH:28]=2)[CH2:33]1

Participants

4

Reactant 2

HCID 198037DimethylpiperazineHCID 136344749HCID 136344749, compound

Product 1

HCID 136186311HCID 136186311, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(9-(4-fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzaldehyde (200 mg, 0.52 mmol), 1,2-dimethylpiperazine (311 mg, 1.56 mmol) in methylene chloride (10 mL) was stirred at room temperature overnight, then NaBCNH3 (129 mg, 2.08 mmole) was added and the mixture was stirred for another 5 hours. After removal of solvents, the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1 to 1:1) to give the title compound (70 mg, 26%). LC-MS (ESI) m/z: 484 (M+1)+. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.43 (d, J=5.2 Hz, 3H), 2.84 (s, 3H), 3.29 (m, 1H), 3.33-3.44 (m, 6H), 4.03 (s, 2H), 4.22 (m, 1H), 4.65 (m, 1 H), 6.91 (m, 1H), 6.97 (m, 1H), 7.00 (d, J=8 Hz, 2H), 7.23-7.37 (m, 4H), 7.65 (m, 1H), 7.77 (d, J=7.2 Hz, 1H), 9.92 (s, 1H).

Workup

  1. additionNaBCNH3 (129 mg, 2.08 mmole) was added
  2. stirringthe mixture was stirred for another 5 hours
  3. customAfter removal of solvents
  4. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-f98b3a0ceb254de5ac05a4a3939148a5
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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