HCID 136374676, compound → HCID 136186306, compound

HRID 1467686Notes

Reaction equation

HRID 1467686 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[NH:33][C:31]4[C:32]5[C:23](=[N:24][NH:25][C:26](=[O:34])[C:27]=5[CH:28]=[CH:29][CH:30]=4)[CH:22]3[C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH3:42])=O)(C)(C)C>Cl.C(#N)C>[F:41][C:38]1[CH:37]=[CH:36][C:35]([CH:22]2[C:23]3=[N:24][NH:25][C:26](=[O:34])[C:27]4[CH:28]=[CH:29][CH:30]=[C:31]([C:32]=43)[NH:33][CH:21]2[C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH:9]([CH3:42])[CH2:10]3)=[CH:16][CH:17]=2)=[CH:40][CH:39]=1

Participants

3

Reactant 1

HCID 136374676HCID 136374676, compound

Product 1

HCID 136186306HCID 136186306, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 22261314Acetonitrile--hydrogen chloride (1/1)Solvent

Procedure

A mixture of tert-butyl-4-(4-(9-(4-fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzyl)-2-methylpiperazine-1-carboxylate (70 mg, 0.123 mole) in 2 ml of HCl-acetonitrile was stirred for 2 hours. Concentrated and the residue was purified by prep-HPLC to afford the title produce as a white solid (30 mg, yield 52%). 1H-NMR (400 MHz, DMSO-d) δ (ppm): 0.87 (d, J=6.4 Hz, 3H), 1.49 (t, J=10 Hz, 1H), 1.83 (t, J=10 Hz, 1H), 2.55 (m, 2H), 2.64 (m, 2H), 2.75 (m, 1H), 3.32 (s, 3H), 4.34 (d, J=9.2 Hz, 1H), 4.72 (d, J=9.2 Hz, 1H), 6.97-7.01 (m, 2H), 7.13-7.24 (m, 7H), 7.37-7.41 (m, 2H), 7.55-7.59 (m, 1H), 12.15 (s, 1H); LC-MS (ESI) m/z: 470 (M+1)+.

Workup

  1. concentrationConcentrated
  2. customthe residue was purified by prep-HPLC
  3. customto afford the title

Sources & evidence

ORD record
ord-aec8bb7dfd4147d7be21cb539bef093b
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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