Diisopropylethylamine → HCID 178436929, compound

HRID 340053Notes

Reaction equation

HRID 340053 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3[NH:16][C:17]([C:19]4[C:27]5[C:22](=[CH:23][C:24]([C:28]6[CH:33]=[C:32]([F:34])[C:31]([OH:35])=[CH:30][C:29]=6[CH2:36][CH3:37])=[CH:25][CH:26]=5)[NH:21][N:20]=4)=[N:18][C:12]=3[CH2:11]2)=[O:9])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:47]([O:51][C:52]([N:54]1[C@@H:59]([CH3:60])[CH2:58][NH:57][CH2:56][C@H:55]1[CH3:61])=[O:53])([CH3:50])([CH3:49])[CH3:48]>CS(C)=O>[C:47]([O:51][C:52]([N:54]1[C@@H:59]([CH3:60])[CH2:58][N:57]([C:2]2[CH:7]=[N:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][C:13]4[NH:16][C:17]([C:19]5[C:27]6[C:22](=[CH:23][C:24]([C:28]7[CH:33]=[C:32]([F:34])[C:31]([OH:35])=[CH:30][C:29]=7[CH2:36][CH3:37])=[CH:25][CH:26]=6)[NH:21][N:20]=5)=[N:18][C:12]=4[CH2:11]3)=[O:9])=[CH:4][N:3]=2)[CH2:56][C@H:55]1[CH3:61])=[O:53])([CH3:50])([CH3:48])[CH3:49]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21021901tert-Butyl (2R,6S)-2,6-dimethylpiperazine-1-carboxylateHCID 178436919HCID 178436919, compound

Product 1

HCID 178436929HCID 178436929, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirring solution of (5-chloropyrazin-2-yl)(2-(6-(2-ethyl-5-fluoro-4-hydroxyphenyl)-1H-indazol-3-yl)-6,7-dihydro-1H-imidazo[4,5-c]pyridin-5(4H)-yl)methanone (150 mg, 0.154 mmol) in DMSO (1.5 mL) were added DIPEA (0.143 mL, 0.87 mmol) and (2R,6S)-2,6-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester (124 mg, 0.58 mmol) and the mixture stirred at room temperature for 18 hours. The crude reaction mass was purified by prep-HPLC Method F to afford (3R,5S)-5′-{2-[6-(2-Ethyl-5-fluoro-4-hydroxy-phenyl)-1H-indazol-3-yl]-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carbonyl}-3,5-dimethyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester as an off white solid (80 mg, 40%).

Workup

  1. customThe crude reaction mass
  2. customwas purified by prep-HPLC Method F

Sources & evidence

ORD record
ord-cfb027b3da344b40ace911dcbda8ee06
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

Loading…