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Diisopropylethylamine → HCID 86699393, compound

HRID 1777556
Notes
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Reaction equation

HRID 1777556 reaction equation
FC1C=C(N(C)[C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)C=CC=1.Cl.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH2:32].CN(C(ON1N=N[C:43]2[CH:44]=[CH:45][CH:46]=N[C:42]1=2)=[N+](C)C)C.[F:50][P-](F)(F)(F)(F)F.C(N([CH2:64][CH3:65])C(C)C)(C)C>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH2:30][CH2:31][NH:32][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:42][C:43]2[CH:65]=[CH:64][CH:46]=[C:45]([F:50])[CH:44]=2)=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

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 132411752-(5-bromo-1H-indol-3-yl)ethan-1-amine hydrochlorideHCID 61984652HCID 61984652, compound

Product 1

HCID 86699393HCID 86699393, compound
Yield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((3-fluorophenyl)(methyl)amino)benzoic acid (0.250 g, 1.09 mmol), 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (0.300 g; 1.09 mmol), HATU (0.414 g; 1.09 mmol) and N,N-diisopropylethylamine (0.469 mL; 2.72 mmol) in DMF (7 mL), was stirred at room temperature for 72 hours. The reaction mixture was then partitioned between ethyl acetate and sodium hydrogen sulfate and the organic layer was successively washed with a saturated aqueous solution of sodium carbonate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) to afford 0.395 g (81%) of the title compound as a white solid.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was successively washed with a saturated aqueous solution of sodium carbonate and brine
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe crude material was purified by flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-f0c5dfb5f4844f5fbe3d0855ff3a9a81
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266832B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes