Sodium Carbonate → HCID 73426448, compound

HRID 1507558Notes

Reaction equation

HRID 1507558 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([OH:9])=O.[NH2:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH3:23])([CH3:22])[C:16](=[O:21])[N:17]2[CH3:20])=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]([NH:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH3:23])([CH3:22])[C:16](=[O:21])[N:17]2[CH3:20])=[CH:13][CH:12]=1)=[O:9]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 529112486-Amino-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 73426448HCID 73426448, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-1H-imidazole-2-carboxylic acid (99.4 mg, 788 μmol) and 6-amino-1,3,3-trimethylindolin-2-one (100 mg, 526 μmol) in DMF (3 ml) were added HATU (400 mg, 1.05 mmol) and DIPEA (347 mg, 468 μl, 2.63 mmol). The reaction mixture was stirred for 3 hours at room temperature and then poured into ethyl acetate and 1 M aqueous sodium carbonate solution. The aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by silica gel chromatography using ethyl acetate/heptane as eluent followed by reversed phase preparative HPLC. The title compound was obtained as off-white crystals (135 mg).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ae0a3ff2b1c24a64a750c29710c90868
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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