HCID 136374713, compound → HCID 136265175, compound

HRID 907989Notes

Reaction equation

HRID 907989 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:43]=[CH:42][C:25]([CH2:26][N:27]3[CH2:32][C@@H:31]([CH3:33])[N:30](C(OC(C)(C)C)=O)[C@H:29]([CH3:41])[CH2:28]3)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1>Cl.CC#N>[CH3:33][CH:31]1[NH:30][CH:29]([CH3:41])[CH2:28][N:27]([CH2:26][C:25]2[CH:42]=[CH:43][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:23][CH:24]=2)[CH2:32]1

Participants

3

Reactant 1

HCID 136374713HCID 136374713, compound

Product 1

HCID 136265175HCID 136265175, compoundYield 56.9%

Reagents, catalysts & solvents 1

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

Procedure

A mixture of (2R,6R)-tert-butyl 4-(4-(9-(4-fluorophenyl)-3-oxo-3,7,8,9-tetrahydro-2H-pyrido[4,3,2-de]phthalazin-8-yl)benzyl)-2,6-dimethylpiperazine-1-carboxylate (72 mg, 0.12 mmol) in HCl—CH3CN (2 mL) was stirred for 2 hours. After removal of solvents, the residue was purified by prep-HPLC to afford the title product as a white solid (33 mg, 53%). LC-MS (ESI) m/z: 497 (M+1)+. 1H-NMR (400 MHz, DMSO) δ (ppm): 1.02-1.03 (d, J=6.4 Hz, 6H), 1.58 (t, J=10 Hz, 1H), 2.66 (d, J=10 Hz, 1H), 2.91 (t, J=6.8 Hz, 2H), 3.41 (s, 2H), 4.20 (d, J=10 Hz, 1H), 4.58 (d, J=10 Hz, 1H), 4.98 (s, 1H), 6.97 (t, J=2.4 Hz, 2H), 7.04 (d, J=8.0 Hz, 1H), 7.09 (d, J=2.4 Hz, 2H), 7.16 (d, J=2.4 Hz, 2H), 7.58 (t, J=7.6 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 10.34 (s, 1H).

Workup

  1. customAfter removal of solvents
  2. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-7451187dc67d4bdab918813f8d43ce9f
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

Loading…