Butylamine → HCID 69375734, compound

HRID 1019281Notes

Reaction equation

HRID 1019281 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([OH:14])=O)=[CH:2]1.[N:21]1(OC(N(C)C)=[N+](C)C)[C:25]2C=C[CH:28]=[CH:29][C:24]=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(N)CCC>>[CH2:25]([NH:21][C:12](=[O:14])[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)[CH2:24][CH2:29][CH3:28]

Participants

6

Reactant 5

HCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 69375012HCID 69375012, compound

Product 1

HCID 69375734HCID 69375734, compoundYield 41%

Procedure

To a solution of 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid (100 mg, 0.3784 mmol.) in 2 ml of DMFd were added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoborate (121.5 mg, 0.3784 mmol.), N-hydroxybenzotriazole (51.1 mg, 0.3784 mmol) and N,N-diisopropylethylamine (129.2 μl, 0.7568 mmol). After stirring at room temperature for 30 min., 34.5 μl (0.3784 mmol.) of n-butylamine were added and the obtained solution was stirred at room temperature, for 24 hours. The resulting mixture was concentrated by evaporation of the solvent in vacuo, the residue was diluted with dichloromethane washed with 1 N NaOH, 1 N HCl, brine, dried over sodium sulphate and evaporated. The residual solid was triturated with Et2O to afford 49 mg of the title compound as a white solid (yield 41%) m.p. 177-179° C. (dec.)

Workup

  1. stirringthe obtained solution was stirred at room temperature, for 24 hours
  2. concentrationThe resulting mixture was concentrated by evaporation of the solvent in vacuo
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with 1 N NaOH, 1 N HCl, brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residual solid was triturated with Et2O

Sources & evidence

ORD record
ord-793ca2fb071a4f5393c80aa6fde574b7
Source dataset
uspto-grants-2002_11
Patent number
US06486322B1

Reaction notes

Loading…