Hydrochloric Acid → 2,2,2-Trifluoro-N-(2-methoxyethyl)-N-[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]acetamide

HRID 2228746Notes

Reaction equation

HRID 2228746 reaction equation
O.OC1C2N=NNC=2C=CC=1.Cl.[CH3:13][O:14][CH2:15][CH2:16][N:17]([CH2:24][C:25]1[CH:26]=[C:27]([CH:43]=[CH:44][CH:45]=1)[CH2:28][CH2:29][NH:30][C:31]1[C:32](=[O:42])[N:33]([CH2:38][C:39](O)=[O:40])[C:34]([CH3:37])=[CH:35][N:36]=1)[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20].CN1CCOCC1.[CH3:53][C:54]1[C:62]2[C:57](=[CH:58][CH:59]=[C:60]([CH2:63][NH2:64])[CH:61]=2)[NH:56][CH:55]=1>CN(C)C=O>[F:21][C:19]([F:20])([F:22])[C:18]([N:17]([CH2:16][CH2:15][O:14][CH3:13])[CH2:24][C:25]1[CH:45]=[CH:44][CH:43]=[C:27]([CH2:28][CH2:29][NH:30][C:31]2[C:32](=[O:42])[N:33]([CH2:38][C:39]([NH:64][CH2:63][C:60]3[CH:61]=[C:62]4[C:57](=[CH:58][CH:59]=3)[NH:56][CH:55]=[C:54]4[CH3:53])=[O:40])[C:34]([CH3:37])=[CH:35][N:36]=2)[CH:26]=1)=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 184708942-[3-[(3-{[(2-methoxyethyl)(2,2,2-trifluoroacetyl)amino]methyl}phenethyl)amino]-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 184709502,2,2-Trifluoro-N-(2-methoxyethyl)-N-[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)benzyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxybenzotriazole hydrate (60 mg, 0.44 mmol) and WSCDl.HCl (93 mg, 0.47 mmol) were added to a solution of 2-[3-[(3-{[(2-methoxyethyl)(2,2,2-trifluoroacetyl)amino]methyl}phenethyl)amino]-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (190 mg, 0.40 mmol) [see preparation 44] in N,N-dimethylformamide (3.0 ml). N-methylmorpholine (123 mg, 1.2 mmol) was added followed by (3-methyl-1H-indol-5-yl)methylamine (72 mg, 0.45 mmol) [see preparation 36]. The reaction mixture was stirred at room temperature for 18 hrs, after which time the mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with water (3×30 ml), brine (30 ml) and dried over MgSO4 and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (99:1:0.1) changing to (98:2:0.2) to afford the title compound as a oil, 113 mg (53%).

Workup

  1. customafter which time the mixture was partitioned between ethyl acetate (30 ml) and water (30 ml)
  2. washThe organic layer was washed with water (3×30 ml), brine (30 ml)
  3. dry with materialdried over MgSO4
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-6e01c48b58e646b5a62b49dc198951ed
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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