HCID 136200379, compound → HCID 178480387, compound

HRID 929107Notes

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-f8f7b321486a47c2bd1cb38ab87f5a5a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290503B2

Reaction notes

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