Potassium Carbonate → HCID 68650500, compound

HRID 646709Notes

Reaction equation

HRID 646709 reaction equation
[NH2:1][C:2]1[C:3]([C:22]([NH:24][CH3:25])=[O:23])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][C@@H:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)=[O:15])[CH:9]=2)=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1>C(#N)C>[Cl:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH:1][C:2]2[C:3]([C:22]([NH:24][CH3:25])=[O:23])=[N:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][C@@H:17]4[CH2:21][CH2:20][N:19]([CH2:37][C:36]5[CH:39]=[CH:40][C:33]([Cl:32])=[CH:34][CH:35]=5)[CH2:18]4)=[O:15])[CH:9]=3)=[CH:6][N:7]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 68651607HCID 68651607, compound

Product 1

HCID 68650500HCID 68650500, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-amino-N-methyl-6-(3-{[(3R)-pyrrolidin-3-ylamino]carbonyl}phenyl)pyrazine-2-carboxamide (34.0 mg, 0.1 mmol) in acetonitrile was added K2CO3 (27.6 mg, 0.2 mmol) followed by 4-chlorobenzyl bromide (30.7 mg, 0.15 mmol). The mixture was allowed to stir at room temperature over 12 h and filtered. The acetonitrile solution was evaporated to dryness, the residue was chromatographed on silica gel using ethyl acetate/hexane 4:1 v/v and trituration of the resulting solid with hexane afforded 3-{[(4-chlorophenyl)methyl]amino}-6-{3-[({(3R)-1-[(4-chlorophenyl) methyl]pyrrolidin-3-yl}amino)carbonyl]phenyl}-N-methylpyrazine-2-carboxamide (28 mg, 47.6%yield): 1H NMR (400 MHz; DMSO-D6): 8.9 (s, 1H); 8.85 (m, 1H); 8.75 (m, 1H); 8.38 (m, 2H); 7.78-7.5 (m, 1H); 4.63 (m, 5H); 3.9 (m, 1H); 3.6 (m, 2H); 3.4 (m, 1H); 2.85 (d, 3H); 2.5 (m, 1H); 2.2 (m, 1H); MS (EI) for C31H30N6O2Cl2: 589 (MH+)

Workup

  1. filtrationfiltered
  2. customThe acetonitrile solution was evaporated to dryness
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-11052ad4188c4aa8a79da9d42f2eb1a4
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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