Water → HCID 15343572, compound

HRID 2924Notes

Reaction equation

HRID 2924 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11][CH3:12])[C:5]=1[N:13]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]([CH2:16][NH2:17])=[O:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.O.[CH3:58][O:59][C:60]([CH2:62][N:63]1[C:71]2[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:65]=[C:64]1[C:72](O)=[O:73])=[O:61]>CN(C)C=O>[CH3:58][O:59][C:60](=[O:61])[CH2:62][N:63]1[C:71]2[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:65]=[C:64]1[C:72](=[O:73])[NH:17][CH2:16][C:14](=[O:15])[N:13]([C:5]1[C:6]([O:11][CH3:12])=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[O:3][CH3:2])[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 112877301-(Methoxycarbonylmethyl)-2-indolecarboxylic acidHCID 18936487HCID 18936487, compound2×

Product 1

HCID 15343572HCID 15343572, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 9 of [(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride (compound 100) is dissolved in 10 ml of dimethylformamide and 0.58 g of 1-(methoxycarbonylmethyl)-2-indolecarboxylic acid, 1.12 g of BOP and then, dropwise, 0.75 g of triethylamine are successively added to the reaction mixture at room temperature. The reaction mixture is left at room temperature for 20 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are washed with water and then dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a yellow oil which is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain white crystals of methyl{2-[[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylcarbamoyl]-1-indolyl}acetate; M.p.=141° C.; Yield: 91%.

Workup

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. washThe organic extracts are washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customleaves a yellow oil which
  6. customis purified by flash chromatography on a column of silica gel, eluent

Sources & evidence

ORD record
ord-6a783fb8430848938491e8e735db7b30
Source dataset
uspto-grants-1998_03
Patent number
US05731340

Reaction notes

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