Dichloromethane → N-(4-(Cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamide

HRID 1400233Notes

Reaction equation

HRID 1400233 reaction equation
[OH:1][CH:2]([CH:6]([NH:14][C:15](=[O:33])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][C:17]=1[C:22]1[N:23]=[C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:25][CH:26]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](O)=[O:4].[CH:34]1([NH2:37])[CH2:36][CH2:35]1.ClCCl.CCN(C(C)C)C(C)C>>[CH:34]1([NH:37][C:3](=[O:4])[CH:2]([OH:1])[CH:6]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]=2[C:22]2[N:23]=[C:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:25][CH:26]=2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 675402612-Hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoic acid

Product 1

HCID 67539859N-(4-(Cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamideYield 90.9%

Conditions

Temperature
5 °C

Procedure

To a solution of 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoic acid (230 mg, 0.501 mmol) and cyclopropylamine (40 μL, 0.570 mmol) in dichloromethane (30 ml) 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate (HATU) (230 mg, 0.605 mmol) and DIPEA (100 μL, 0.605 mmol) were added at 5° C. The mixture was stirred for 1 hour at 5° C. and then for 5 hours at room temperature. The mixture was concentrated under reduced pressure, 40 ml of water added, the precipitate formed filtered off with suction, washed with water and dried in vacuo to give 227 mg of a white amorphous solid;

Workup

  1. waitfor 5 hours at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure, 40 ml of water
  3. additionadded
  4. customthe precipitate formed
  5. filtrationfiltered off with suction
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a7dcb32f585b41029e94c8185d4ca6a4
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

Loading…