Trifluoroacetic acid → HCID 68651607, compound

HRID 646708Notes

Reaction equation

HRID 646708 reaction equation
CC([CH:5]1[CH:9]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[N:23][C:22]([NH2:25])=[C:21]([C:26]([NH:28][CH3:29])=[O:27])[N:20]=3)[CH:14]=2)=[O:12])[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:25][C:22]1[C:21]([C:26]([NH:28][CH3:29])=[O:27])=[N:20][C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([C:11]([NH:10][C@@H:9]3[CH2:8][CH2:7][NH:6][CH2:5]3)=[O:12])[CH:14]=2)=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86607838HCID 86607838, compound

Product 1

HCID 68651607HCID 68651607, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl-3-{[(3-{5-amino-6[(methylamino)carbonyl )pyrazin-2-yl}phenyl}carbonyl}amino}pyrrolidine-1-carboxylate (0.7 g, mmol) was suspended in dichloromethane (4 mL) and TFA (3 mL) was added. The mixture was stirred at ambient temperature for 2 hr. After removal of volatiles under reduced pressure, the residue was partitioned between saturated solution K2CO3 (300 mg) and dichloromethane (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated to dryness to afford 0.4 g (74% yield) of 3-amino-N-methyl-6-(3-{[(3R)-pyrrolidin-3-ylamino]carbonyl}phenyl) pyrazine-2-carboxamide. 1H NMR (400 MHz; DMSO-D6): 8.9 (s, 1H); 8.85 (m, 1H); 8.71 (d, 1H); 8.48 (m, 1H); 7.4 (d, 1H); 7.84 (d, 1H); 7.6 (t, 1H); 4.54 (m, 2H); 3.6-3.18 (m, 4H); 2.85 (d, 3H); 2.25 (m, 1H); 2.1 (m, 1H); MS (EI) for C17H20N6O2: 341 (MH+)

Workup

  1. customAfter removal of volatiles under reduced pressure
  2. customthe residue was partitioned between saturated solution K2CO3 (300 mg) and dichloromethane (10 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0223abc9534042d6abcb8ea797dd504f
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…