Trifluoroacetic acid → HCID 57947540, compound

HRID 416386Notes

Reaction equation

HRID 416386 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C@H:16]([N:33]([CH3:46])[C:34]([NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=1[Cl:45])=[O:35])[CH2:17][O:18][C:19](=[O:32])[NH:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([F:31])=[CH:26][CH:25]=2)=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:31][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[N:22][C:21]([NH:20][C:19](=[O:32])[O:18][CH2:17][C@@H:16]([N:33]([CH3:46])[C:34]([NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=1[Cl:45])=[O:35])[CH2:15][CH2:14][CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH2:8])=[CH:30]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57947854HCID 57947854, compound

Product 1

HCID 57947540HCID 57947540, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-Fluoro-isoquinolin-3-yl)-carbamic acid (S)-5-(2-tert-butoxycarbonylamino-acetylamino)-2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-pentyl ester (105 mg, 0.16 mmol) in DCM (10.0 mL) was added TFA (1.0 mL). The mixture was stirred at RT for 2 h. The mixture was concentrated and re-dissolved DCM. The DCM layer was washed with K2CO3 (2 N), saturated NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified on silica gel column using a mixture of DCM and MeOH to give (S)-5-(2-aminoacetamido)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 6-fluoroisoquinolin-3-ylcarbamate (71 mg, 79%). LRMS (M+H+) m/z 563.2.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionre-dissolved DCM
  3. washThe DCM layer was washed with K2CO3 (2 N), saturated NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel column
  8. additiona mixture of DCM and MeOH

Sources & evidence

ORD record
ord-7ea49ae54bc4412988e497194073299a
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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