Diisopropylethylamine → HCID 18002310, compound

HRID 478928Notes

Reaction equation

HRID 478928 reaction equation
FC1[CH:3]=[C:4]2[C:8](=CC=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[C:13]1(C)[C:17](C(O)=O)=[CH:16][NH:15][CH:14]1/[CH:21]=[C:22]1\[C:23](=[O:32])[NH:24][C:25]2[C:30]\1=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2.CN(C([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:58][CH2:59][N:60](C(C)C)[CH:61]([CH3:63])[CH3:62]>CN(C=O)C.C(Cl)(Cl)Cl>[CH3:5][CH:4]1[CH:8]([N:60]2[CH:61]([CH3:63])[CH2:62][O:41][CH2:58][CH2:59]2)[N:7]([C:6](/[C:21](/[C:14]2[NH:15][CH:16]=[CH:17][CH:13]=2)=[C:22]2\[C:23](=[O:32])[NH:24][C:25]3[C:30]\2=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:11])[CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86588161HCID 86588161, compound

Product 1

HCID 18002310HCID 18002310, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1-(8-Azabenztriazolyl)-ester of (3Z)-3-({3,5-dimethyl-4-carboxy]1-H-pyrrol-2-yl}methylene)-5-fluoro-1.3-dihydro-2H-indol-2-one (0.5 mmol, 210 mg) [prepared by activating (3Z)-3-(3,3-dimethyl-4-carboxy-1-H-pyrrol-2-ylmethylene)-5-fluoro-1.3-dihydro-2H-indol-2-one (480 mg; 1.6 mmol) with the HATU reagent (570 mg, 1.5 mmol) in the presence of Hunig base (3.0 mmol, 0.525 ml) in DMF (5ml) and isolated in pure form by precipitation with chloroform (5 ml) and drying on high vacuum in 92% yield (579 mg)] was suspended in anhydrous DMA (1.0 ml). A solution of 4-(azetidin-3-yl)-morpholine; (142.5 mg, 1 mmol) in anhydrous DMA (1.0 ml) was added in one portion and the obtained solution was stirred at room temperature for 20 min. The reaction mixture was evaporated at room temperature using an oil pump, the thick residue was diluted with 6 ml of a mixture of methanol plus diethyl amine (20:1; v/v), inoculated mechanically and placed into a refrigerator (+3° C.) for 8 hours. The precipitates were filtered (with a brief wash with an ice-cold methanol) and dried on high vacuum to give the desired product. 71.5% yield (152 mg of an orange solid)

Workup

  1. customdrying on high vacuum in 92% yield (579 mg)]
  2. addition(142.5 mg, 1 mmol) in anhydrous DMA (1.0 ml) was added in one portion
  3. customThe reaction mixture was evaporated at room temperature
  4. additionthe thick residue was diluted with 6 ml of a mixture of methanol plus diethyl amine (20:1; v/v)
  5. waitplaced into a refrigerator (+3° C.) for 8 hours
  6. filtrationThe precipitates were filtered (with
  7. washa brief wash with an ice-cold methanol) and
  8. customdried on high vacuum

Sources & evidence

ORD record
ord-ecbf778c5c0c45bfa0443ce42ddd9106
Source dataset
uspto-grants-2003_11
Patent number
US06642232B2

Reaction notes

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