Dichloromethane → HCID 67520760, compound

HRID 1926155Notes

Reaction equation

HRID 1926155 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14]([NH:16][CH2:17][CH2:18][N:19]2[C:27]3[C:26]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][C:36]5[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=5)=[C:31]([CH3:46])[CH:30]=4)=[N:25][CH:24]=[N:23][C:22]=3[CH:21]=[CH:20]2)=[O:15])[CH2:3]1.FC(F)(F)C(O)=O.[Cl:54]CCl>>[ClH:54].[ClH:54].[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([NH:16][CH2:17][CH2:18][N:19]2[C:27]3[C:26]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][C:36]5[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:43])([F:44])[F:45])[CH:37]=5)=[C:31]([CH3:46])[CH:30]=4)=[N:25][CH:24]=[N:23][C:22]=3[CH:21]=[CH:20]2)=[O:15])[CH2:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57597329HCID 57597329, compound

Product 1

HCID 67520760HCID 67520760, compound

Procedure

tert-Butyl (2S,4R)-4-hydroxy-2-[({2-[4-({3-methyl-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}amino)carbonyl]pyrrolidine-1-carboxylate (230 mg) was dissolved in dichloromethane (2.39 mL), trifluoroacetic acid (1.79 mL) was added, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate/tetrahydrofuran (1:1, 50 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (30 mL), dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to basic silica gel chromatography (ethyl acetate/methanol=100/0→80/20). The fractions containing the title compound were collected and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, 4N hydrochloric acid (0.252 mL) was added, and the mixture was crystallized to give the title compound (136 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate/tetrahydrofuran (1:1, 50 mL)
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (30 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe fractions containing the title compound
  7. customwere collected
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. addition4N hydrochloric acid (0.252 mL) was added
  11. customthe mixture was crystallized

Sources & evidence

ORD record
ord-41a37a4aa7a547bf99b49cfdc176d89d
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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