Hydrochloric Acid → HCID 57947911, compound

HRID 340917Notes

Reaction equation

HRID 340917 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-8a340f90065343b6a1fff07a9711a5c1
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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