Diisopropylethylamine → HCID 12018604, compound

HRID 2301847Notes

Reaction equation

HRID 2301847 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][C:12]2[CH:18]=[C:17]([NH:19][C:20](=[O:22])[CH3:21])[CH:16]=[CH:15][C:13]=2[NH2:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34](O)=[O:35])[CH:32]=2)[CH:27]=[CH:26]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)C(C)C)(C)C>ClCCl.CN(C=O)C>[C:20]([NH:19][C:17]1[CH:18]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:23]=[CH:24][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)[C:13]([NH:14][C:34]([C:31]2[CH:32]=[C:33]3[C:28]([CH:27]=[CH:26][NH:25]3)=[CH:29][CH:30]=2)=[O:35])=[CH:15][CH:16]=1)(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5952301H-indole-6-carboxylic acidHCID 2733179PyBroPHCID 18373188HCID 18373188, compound

Product 1

HCID 12018604HCID 12018604, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(4-t-butylbenzoyl)amino-4-(acetylamino)aniline (40 mg, 0.12 mmol), 6-indolecarboxylic acid (40 mg, 0.24 mmol) and bromotris(pyrrolidino)phosphonium hexafluorophosphate (112 mg, 0.12 mmol) in dichloromethane (10 mL) and DMF (1 mL) was added N,N-diisopropylethylamine (42 mg, 0.36 mmol). After 3 days, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed once with 1 N HCl, once with satd aq sodium bicarbonate, dried with MgSO4, filtered and concentrated in vacuo. The residue was then chromatographed over silica gel, eluting with 10% methanol/dichloromethane and the product containing fractions were combined and concentrated to give 40 mg (71%) of the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed once with 1 N HCl, once with satd aq sodium bicarbonate
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then chromatographed over silica gel
  8. washeluting with 10% methanol/dichloromethane
  9. additionthe product containing fractions
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6e2379eb738e4acfa63300e196f8b9cf
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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