Ammonia → HCID 10354834, compound

HRID 1376138Notes

Reaction equation

HRID 1376138 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([OH:19])=O)=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.[N:27]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.N.CO>CN(C=O)C.CCOC(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:27])=[O:19])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 101989283-(pyridin-4-ylamino)-1H-indole-2-carboxylic Acid

Product 1

HCID 10354834HCID 10354834, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At −20° C. stir a solution of 3-(pyridin-4-ylamino)-1H-indole-2-carboxylic acid (1.26 g, 3.0 mmol) in DMF (12 mL) and add BOP (1.32 g, 3.0 mmol) and then diisopropylethylamine (0.8 mL, 4.5 mmol). Stir the reaction for 0.25 h and add a solution of 7M NH3 in MeOH (0.43 mL, 3.0 mmol). Allow the reaction to stir at room temperature overnight and add EtOAc. Wash the organic solution with aqueous NaHCO3, brine and dry over MgSO4. Filter and concentrate the filtrate under vacuum to obtain a solid. Recrystallize the solid from EtOAc to obtain 0.425 g of the title compound as a yellow solid: MS 253(M+H); m.p. 230° C. (decomposition); TLC (silica gel, dichloromethane/MeOH/NH4OH, 8:2:0.1 v/v), Rf=0.39.

Workup

  1. customthe reaction for 0.25 h
  2. customthe reaction
  3. stirringto stir at room temperature overnight
  4. washWash the organic solution with aqueous NaHCO3, brine
  5. dry with materialdry over MgSO4
  6. filtrationFilter
  7. concentrationconcentrate the filtrate under vacuum
  8. customto obtain a solid
  9. customRecrystallize the solid from EtOAc

Sources & evidence

ORD record
ord-1d36244a86cf4daea7befadc81a0e666
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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