1-(4-(Trimethylstannyl)phenyl)piperidin-4-ol → (R)-tert-butyl 2-((7-(4-(4-hydroxypiperidin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

HRID 57642Notes

Reaction equation

HRID 57642 reaction equation
C[Sn](C)(C)[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl[C:19]1[N:28]=[C:27]([NH:29][CH2:30][C@H:31]2[O:36][CH2:35][CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]2)[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:15][CH:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:19]3[N:28]=[C:27]([NH:29][CH2:30][C@H:31]4[O:36][CH2:35][CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]4)[C:26]4[C:21](=[N:22][CH:23]=[CH:24][N:25]=4)[CH:20]=3)=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 710936821-(4-(Trimethylstannyl)phenyl)piperidin-4-olHCID 86706988(R)-tert-butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 86717400(R)-tert-butyl 2-((7-(4-(4-hydroxypiperidin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylateYield 27.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1-(4-(trimethylstannyl)phenyl)piperidin-4-ol (398 mg, 1.17 mmol), (R)-tert-butyl 2-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (297 mg, 0.78 mmol), tetrakis(triphenylphosphine)palladium (180 mg, 0.15 mmol) were mixed in 5 mL toluene. The mixture was reacted at 100° C. overnight. Filtrated and concentrated, purified by flash chromatography (PE:EA=1:2) to give 112 mg reddish solid.

Workup

  1. customThe mixture was reacted at 100° C. overnight
  2. filtrationFiltrated
  3. concentrationconcentrated
  4. custompurified by flash chromatography (PE:EA=1:2)

Sources & evidence

ORD record
ord-c0cad0a5575a4ad8be1364d8ccd5a2c8
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…