Water → 3-{2-[[(Cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrile

HRID 2925Notes

Reaction equation

HRID 2925 reaction equation
Cl.[CH:2]1([CH2:8][N:9]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[CH:16][C:15]=2[O:23][CH3:24])[C:10]([CH2:12][NH2:13])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.[CH2:52]([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])[CH3:53].[OH2:59].[CH3:60][N:61](C)C=O>C(CCN1C2C(=CC=CC=2)C=C1C(O)=O)#N>[CH:2]1([CH2:8][N:9]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[CH:16][C:15]=2[O:23][CH3:24])[C:10]([CH2:12][NH:13][C:53]([C:52]2[N:54]([CH2:57][CH2:58][C:60]#[N:61])[C:55]3[C:40]([CH:35]=2)=[CH:39][CH:38]=[CH:37][CH:56]=3)=[O:59])=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18936477[(Cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride2×

Product 1

HCID 189365093-{2-[[(Cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrileYield 91%

Reagents, catalysts & solvents 1

HCID 18936519HCID 18936519, compoundSolvent

Procedure

1.5 g of [(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride (compound 113) are dissolved in 10 ml of dimethylformamide and 0.918 g of 1-(2-cyanoethyl)-2-indolecarboxylic acid, 1.95 g of BOP and then, dropwise, 1.28 g of triethylamine are then successively added. The reaction mixture is left at room temperature for 3 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residue is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain 3-{2-[[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrile in the form of a pasty foam; Yield: 91%.

Workup

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over anhydrous sodium sulphate
  3. customevaporated to dryness
  4. customThe residue is purified by flash chromatography on a column of silica gel, eluent

Sources & evidence

ORD record
ord-3f2f0bb549ae43f2a22173e022628003
Source dataset
uspto-grants-1998_03
Patent number
US05731340

Reaction notes

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