Sodium Carbonate → HCID 73425726, compound

HRID 1507570Notes

Reaction equation

HRID 1507570 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1.[Cl:15][C:16]1[N:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Cl:15][C:16]1[N:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:17]=1[C:18]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][CH:3]=1)=[O:19]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 1217242-Chloro-6-methylnicotinic 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 73425726HCID 73425726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-amino-1,3,3-trimethylindolin-2-one (120 mg, 631 μmol), 2-chloro-6-methylnicotinic acid (108 mg, 631 μmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (480 mg, 1.26 mmol) and N,N-diisopropylethylamine (408 mg, 536 μl, 3.15 mmol) in DMF (3 ml) was stirred at room temperature for 16 hours. An aqueous solution of Na2CO3 was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as white solid (167 mg).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-f7f05e4ee7624bc386952247e1ea77ef
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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