Hydrochloric Acid → HCID 57947911, compound

HRID 409779Notes

Reaction equation

HRID 409779 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:44])[O:14][CH2:15][C@@H:16]([N:30]([CH3:43])[C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=1[Cl:42])=[O:32])[CH2:17][NH:18][C:19](=[O:29])[CH2:20][NH:21]C(OC(C)(C)C)=O)=[CH:5]2.C(O)(C(F)(F)F)=O.Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:44])[O:14][CH2:15][C@@H:16]([N:30]([CH3:43])[C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=1[Cl:42])=[O:32])[CH2:17][NH:18][C:19](=[O:29])[CH2:20][NH2:21])=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57947374HCID 57947374, compound

Product 1

HCID 57947911HCID 57947911, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(2-tert-butoxycarbonylaminoacetamido)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)propyl 6-fluoroisoquinolin-3-ylcarbamate (0.87 g, 1.37 mmol) in DCM (30.0 mL) was added TFA (3.0 mL). The mixture was stirred for 1 h. The mixture was concentrated and dissolved in EtOAc. The EtOAc solution was washed with Na2CO3, brine, dried over Na2SO4, and filtered. To the filtrate was added HCl (4 M in dioxane, 0.7 mL, 2.8 mmol). The organic solvent was removed under reduced pressure to give (S)-3-(2-aminoacetamido)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)propyl 6-fluoroisoquinolin-3-ylcarbamate (730 mg, 93%) as a HCl salt. LRMS (M+H+) m/z 535.2.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with Na2CO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d26b40129a744cf39a4b2fbab7345ccf
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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