Diisopropylethylamine → HCID 57901655, compound

HRID 1851496Notes

Reaction equation

HRID 1851496 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[F:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[CH:29]=1)[C:24](O)=[O:25].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.CN(C)C=O>[F:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[CH:29]=1)[C:24]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2)=[O:25]

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 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 67109493HCID 67109493, compound

Product 1

HCID 57901655HCID 57901655, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 7-amino-1H-indole-2-carboxylate (210 mg), 3,5-bis[(2-fluorobenzyl)oxy]benzoic acid (380 mg), ethyldiisopropylamine (0.47 mL), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (510 mg) and N,N-dimethylformamide (8 mL) was stirred at 60° C. for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane and dissolved in ethyl acetate (50 mL). Activated carbon was added, and the mixture was stirred at 60° C. for 30 min. The activated carbon was filtered off, and the filtrate was concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (284 mg, yield 50%) as colorless crystals. melting point 157-158° C.

Workup

  1. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained crystals were washed with ethyl acetate-hexane
  5. dissolutiondissolved in ethyl acetate (50 mL)
  6. additionActivated carbon was added
  7. stirringthe mixture was stirred at 60° C. for 30 min
  8. filtrationThe activated carbon was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-7d79a0e1141f465a8997378437289dc1
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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