HCID 136200379, compound → HCID 178480387, compound

HRID 2361163Notes

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-55550009e9e24f3f81c97f6241a6a4fd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686005B2

Reaction notes

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