Triphenylphosphine → 3-[2-[1-(t-Butoxycarbonyl)piperidin-4-ylmethoxy]-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

HRID 1434847Notes

Reaction equation

HRID 1434847 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:16]([NH:17][C:18](=[S:27])[C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=3[OH:26])=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[N:6][CH:7]=1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH2:41]O)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([CH2:41][O:26][C:20]2[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:19]=2[C:18]([NH:17][C:16]2[C:11]([C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])=[N:12][CH:13]=[CH:14][CH:15]=2)=[S:27])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 136348818N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide

Product 1

HCID 866200053-[2-[1-(t-Butoxycarbonyl)piperidin-4-ylmethoxy]-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide (750 mg, 1.8 mmol), 1-t-butoxycarbonyl-4-hydroxymethylpiperidine (387 mg, 1.8 mmol), triphenylphosphine (568 mg, 2.26 mmol) and DMF (9 mL) was added DEAD (0.36 mL, 2.26 mmol), and the mixture was stirred for 18 h. The reaction mixture was concentrated and chromatographed (CH2Cl2; 10% EtOAc/CH2Cl2) to give the desired product as a white solid (950 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed (CH2Cl2; 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-5b930d7723b94925ad8bf370dfbbbbdc
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

Loading…