HCID 136374676, compound → HCID 136186306, compound

HRID 907948Notes

Reaction equation

HRID 907948 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:42]=[CH:41][C:25]([CH2:26][N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH:29]([CH3:40])[CH2:28]3)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1>Cl.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][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:42]=[CH:41][C:25]([CH2:26][N:27]3[CH2:32][CH2:31][NH:30][CH:29]([CH3:40])[CH2:28]3)=[CH:24][CH:23]=2)=[CH:6][CH:7]=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-d6) 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-5553ef9f733247d193625dce556a044d
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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