1-Boc-2,6-dimethylpiperazine → HCID 136374713, compound

HRID 1467727Notes

Reaction equation

HRID 1467727 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][CH:31]1[CH2:36][NH:35][CH2:34][CH:33]([CH3:37])[N:32]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>C(Cl)Cl>[C:41]([O:40][C:38]([N:32]1[C@H:33]([CH3:37])[CH2:34][N:35]([CH2:26][C:25]2[CH:28]=[CH:29][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:23][CH:24]=2)[CH2:36][C@H:31]1[CH3:30])=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 222199261-Boc-2,6-dimethylpiperazineHCID 136344749HCID 136344749, compound

Product 1

HCID 136374713HCID 136374713, compoundYield 24%

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, 520 mmol), tert-butyl 2,6-dimethylpiperazine-1-carboxylate (335 mg, 1.56 mmol) in methylene chloride (10 mL) was stirred at room temperature overnight, then NaBCNH3 (129 mg, 2.08 mmol) 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 (72 mg, 24%). LC-MS (ESI) m/z: 584 (M+1)+.

Workup

  1. additionNaBCNH3 (129 mg, 2.08 mmol) 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-1c0a6684f24a4b72a3430e0ee57d16b7
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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