Citric Acid → methyl 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate

HRID 1909870Notes

Reaction equation

HRID 1909870 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17](O)=[O:18])[CH:10]=[CH:9]2)=[CH:3][CH:2]=1.Cl.[NH2:27][C@H:28]([C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1)[CH3:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:27][C@H:28]([C:30]3[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=3)[CH3:29])=[O:18])[CH:10]=[CH:9]2)=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 583069041-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylic acid

Product 1

HCID 58306872methyl 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-(biphenyl-4-ylmethyl)-1H-indole-7-carboxylic acid (0.20 g), methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride, and HATU was added DMF (4.0 mL), followed by adding diisopropylethylamine (0.26 mL) under ice-cooling and then stirring at room temperature for 22 hours. Again, the mixture was ice-cooled, a 10% aqueous citric acid solution (4.0 mL) was added thereto, and the precipitated solid was collected by filtration, washed with water, and dried at 60° C. under reduced pressure to obtain methyl 4-[(1S)-1-({[1-(biphenyl-4-ylmethyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate (0.30 g).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-e3c921bd0eff45f58c46cd40af523623
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

Loading…