Diisopropylethylamine → HCID 70981446, compound

HRID 1475423Notes

Reaction equation

HRID 1475423 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]([OH:20])=O)=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH3:22])([CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[N:39]1(OC(N(C)C)=[N+](C)C)[C:43]2[N:44]=CC=C[C:42]=2N=N1.ONC(=N)C>CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]3[O:20][N:44]=[C:43]([CH3:42])[N:39]=3)=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH3:21])([CH3:22])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70979892HCID 70979892, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 70981446HCID 70981446, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

To 6-chloro-3,3-dimethyl-2,3-dihydro-indole-1,5-dicarboxylic acid 1-tert-butyl ester (0.067 g, 0.21 mmol) in DMF (1.03 mL) was added N,N-diisopropylethylamine (0.126 μL, 0.72 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.08 g, 0.21 mmol) at room temperature. After stirring for 10 minutes, N-hydroxyacetamidine (0.015 g, 0.41 mmol) was added and the reaction stirred for 18 h. DMF (3.44 mL) was added and the reaction heated to 120° C. for 3 h. Water was added and the mixture extracted with diethyl ether (3×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-60%, EtOAc in petrol 40-60) gave the title compound (36 mg). MS: [M+H]+=364.

Workup

  1. stirringthe reaction stirred for 18 h
  2. extractionthe mixture extracted with diethyl ether (3×)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washChromatography (silica gel, gradient elution, 0-60%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-b6c8cc12bf794e1d88aedbc98480f51a
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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