HCID 136200379, compound → HCID 178480387, compound

HRID 561924Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:39])[CH2:9][NH:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C:12]=2[C:18]2[NH:19][C:20]3[C:28]([N:29]=2)=[CH:27][C:26]2[C:25](=[O:30])[N:24]([CH:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[C:23](=O)[C:22]=2[CH:21]=3)[CH:5]=[CH:6][CH:7]=1>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:39])[CH2:9][NH:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[C:12]=2[C:18]2[NH:29][C:28]3[C:20](=[CH:21][C:22]4[CH2:23][N:24]([CH:31]5[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]5)[C:25](=[O:30])[C:26]=4[CH:27]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-{4-[(S)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-(1-methyl-piperidin-4-yl)-1H-1,3,6-triaza-s-indacene-5,7-dione (36.1 mg, 0.066 mmol) was mixed with zinc dust (100 mg) in AcOH (4 mL) and the reaction mixture was heated at 90° C. for 2 h. After it was cooled to the room temperature, the upper clear layer of the reaction mixture was evaporated and the residue was subjected to HPLC purification to afford the title compound in TFA salt form (9.2 mg, 22%). 1H NMR (DMSO-d6) δ 1.90-2.15 (4H), 2.75 (s, 3H, CH3), 3.21 (m, 2H), 3.42-3.60 (2H), 3.65 (m, 1H), 4.31 (m, 1H), 4.50 (s, 2H), 4.98 (m, 1H), 6.19 (d, J=6 Hz, 1H), 7.31-7.41 (3H), 7.51 (d, J=6 Hz, 1H), 7.63 (s, 1H), 7.78 (s, 1H), 7.90 (s, 1H), 9.60 (br s, 1H), 11.06 (br s, 1H, NH), 11.23 (br d, J=6 Hz, 1H, NH); ESI-MS m/z 533.5 (MH+).

Workup

temperatureAfter it was cooled to the room temperature
customthe upper clear layer of the reaction mixture was evaporated
customthe residue was subjected to HPLC purification

Sources & evidence

ORD record: ord-b6d1a0716589404397f9a6042b224150
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063225B2

Reaction notes

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