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Ammonium formate → tert-butyl (2R)-2-({[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}methyl)-1-pyrrolidinecarboxylate

HRID 567825
Notes
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Reaction equation

HRID 567825 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][NH:14][C:15]1[C:16](=[O:26])[N:17]([CH2:22][C:23](O)=[O:24])[C:18]([CH3:21])=[CH:19][N:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([CH2:37][NH2:38])[CH:35]=2)[NH:30][CH:29]=1.C([O-])=O.[NH4+]>[Pd].ClCCl>[CH3:21][C:18]1[N:17]([CH2:22][C:23]([NH:38][CH2:37][C:34]2[CH:35]=[C:36]3[C:31](=[CH:32][CH:33]=2)[NH:30][CH:29]=[C:28]3[CH3:27])=[O:24])[C:16](=[O:26])[C:15]([NH:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 599006292-[3-({[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

Product 1

HCID 59900555tert-butyl (2R)-2-({[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}methyl)-1-pyrrolidinecarboxylateYield 44%

Reagents, catalysts & solvents

2
HCID 23938PalladiumCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by a similar method to preparation 45 from 2-[3-({[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid [see preparation 54] and (3-methyl-1H-indol-5-yl)methylamine (72 mg, 0.45 mmol) [see preparation 36]. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0) changing to (95:5) in 1% increments 1H-NMR indicated starting chloro compound material. A mixture of this product with 10% palladium on charcoal (39.6 mg) and ammonium formate (439.5 mg,6.98 mmol) in dichloromethane (50 ml), was then stirred at room temperature overnight. Additional, 10% Palladium on charcoal (49 mg) was added and the mixture was heated under reflux for 48 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was separated and dried over MgSO4 and the solvent evaporated under reduced pressure to afford the title compound as a off-white solid, (44%).

Workup

  1. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 48 hrs
  4. filtrationafter which time the catalyst was filtered off
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-891a47a3bac841aaaf8d8ead4354b925
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06180627B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes