Diisopropylethylamine → HCID 59762445, compound

HRID 40138Notes

Reaction equation

HRID 40138 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:13]([OH:15])=O)=[CH:10][CH:9]=[C:8]([O:16][CH3:17])[CH:7]=2)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:31][NH2:32].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(Cl)Cl.CCOC(C)=O>[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:31][NH:32][C:13]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH:1]([CH3:2])[CH3:3])=[O:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1235723,4-DifluorobenzylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69226532HCID 69226532, compound2×

Product 1

HCID 59762445HCID 59762445, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-isopropyl-6-methoxy-1H-indole-3-carboxylic acid (Compound 155, 10 mg, 0.046 mmol) in CH2Cl2 (1 ml) was added i-Pr2NEt (17 μl, 0.098 mmol) and 3,4-difluorobenzylamine (11 μl, 0.092 mmol), followed by BOP. After completion, the reaction was diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-8585ed87a7904789bf72711bf2e43075
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

Loading…