Diisopropylamine → HCID 46865821, compound

HRID 2043465Notes

Reaction equation

HRID 2043465 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[CH:12]=[C:13]([CH:17]=[C:18]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[N:19]=2)[C:14]([OH:16])=O)[CH3:9])=[CH:4][CH:3]=1.[CH:27]([NH:30]C(C)C)(C)[CH3:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.Cl.C(N)C>C(OCC)(=O)C.CN(C)C=O>[CH2:27]([NH:30][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[CH:23][N:22]=2)[N:19]=[C:11]([NH:10][C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH3:9])[CH:12]=1)[CH3:28]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 11198Ethylamine hydrochlorideHCID 2724699PyBOPHCID 46865572HCID 46865572, compound

Product 1

HCID 46865821HCID 46865821, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dimethylformamide solution of 450 mg of (S)-2-[1-(4-fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino)isonicotinic acid (Example 141) and 2.2 ml of diisopropylamine was added, 1.32 g of 1H-benzotriazol-1-yloxy tripyrrolidinophosphonium hexafluorophosphate, and the mixture was stirred for 15 minutes. 520 mg of ethylamine hydrochloride was added thereto, and the mixture was stirred for 2 days. The reaction solution was diluted with ethyl acetate, and the organic layer was washed in turn with water and brine, and then dried over magnesium sulfate. The solvent was distilled off, and then the obtained residue was purified by silica gel column chromatography to obtain 390 mg of the objective compound as a pale yellow powder.

Workup

  1. washthe organic layer was washed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-075fe7abfdff4c5ca251864e560013fa
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

Loading…