Sodium cyanoborohydride → HCID 136374676, compound

HRID 1467685Notes

Reaction equation

HRID 1467685 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][CH2:33][N:32]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].[BH3-]C#N.[Na+]>C(Cl)Cl>[C:40]([O:39][C:37]([N:32]1[CH2:33][CH2:34][N:35]([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:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:29][CH:28]=2)[CH2:36][CH:31]1[CH3:30])=[O:38])([CH3:42])([CH3:41])[CH3:43]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateHCID 136344749HCID 136344749, compound

Product 1

HCID 136374676HCID 136374676, 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, 0.52 mmol) and tert-butyl 2-methylpiperazine-1-carboxylate (311 mg, 1.56 mmol) in methylene chloride (10 mL) was stirred at room temperature overnight, then NaBH3CN (129 mg, 2.1 mmol) was added and the mixture was stirred for another 5 hours. Concentrated and the residue was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1 to 1:1) to give the title compound (70 mg, yield 24%). LC-MS (ESI) m/z: 570 (M+1)+.

Workup

  1. stirringthe mixture was stirred for another 5 hours
  2. concentrationConcentrated
  3. customthe residue was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-7cde577087804a658b21730e11d18fdc
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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