Pyridine → Methyl 3-((3-((2-((2-phenylpyrimidin-5-yl)carbamoyl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)thio)propanoate

HRID 2406072Notes

Reaction equation

HRID 2406072 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][CH:12]=1)=[O:5].Cl[C:30]([C:32]1[CH:33]=[C:34]([CH:43]=[CH:44][CH:45]=1)[CH2:35][S:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[O:31].N1C=CC=CC=1>O1CCCC1>[C:13]1([C:10]2[N:11]=[CH:12][C:7]([NH:6][C:4]([C:3]3[CH:19]=[C:20]([N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:21]=[CH:22][C:2]=3[NH:1][C:30]([C:32]3[CH:33]=[C:34]([CH:43]=[CH:44][CH:45]=3)[CH2:35][S:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[O:31])=[O:5])=[CH:8][N:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 665870272-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamideHCID 86705202Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

Product 1

HCID 66587735Methyl 3-((3-((2-((2-phenylpyrimidin-5-yl)carbamoyl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzyl)thio)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide (138 mg, 0.37 mmol, 1.00 equiv) in tetrahydrofuran (6 mL) was added methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate (112 mg, 0.41 mmol, 1.10 equiv) and pyridine (60 mg, 0.76 mmol, 2.00 equiv) and the resulting solution was stirred for 5 h at room temperature. The reaction progress was monitored by LCMS. The crude product was used directly in the next step.

Sources & evidence

ORD record
ord-66280a5bcbb64bd49dc8232011e20201
Source dataset
uspto-grants-2014_08
Patent number
US08809339B2

Reaction notes

Loading…