Trifluoroacetic acid → HCID 57947624, compound

HRID 409789Notes

Reaction equation

HRID 409789 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([O:13][CH2:14][C@@H:15]([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])[CH2:16][CH2:17][C:18]([N:20]1[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]1)=[O:19])=[O:12].C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:12])[O:13][CH2:14][C@@H:15]([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])[CH2:16][CH2:17][C:18](=[O:19])[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57947648HCID 57947648, compound

Product 1

HCID 57947624HCID 57947624, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 4-(5-(benzo[d]thiazol-2-ylcarbamoyloxy)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentanoyl)piperazine-1-carboxylate (713 mg, 1.05 mmol) in DCM (5 mL) was added TFA (1 mL) and allowed to stir for 30 min. The reaction mixture was concentrated, and the residue purified by RP-HPLC (20-100% ACN in H2O) and concentrated to give (S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-oxo-5-(piperazin-1-yl)pentyl benzo[d]thiazol-2-ylcarbamate as an off-white solid (430 mg, 71%). LRMS (M+H+)=577.1

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by RP-HPLC (20-100% ACN in H2O)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6839a9c5d068461b8675bae492725d23
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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