Trifluoroacetic acid → 3-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide

HRID 880311Notes

Reaction equation

HRID 880311 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:31])[CH2:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]([NH:23]C(=O)OC(C)(C)C)[CH:20]=[CH:21][CH:22]=1)=[O:16].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:15]([NH:14][CH2:13][CH:12]([OH:31])[CH2:11][N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90245499tert-butyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)phenyl)carbamate

Product 1

HCID 902415853-amino-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl (3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl) carbamoyl)phenyl)carbamate (500 mg, 1.18 mmol) in DCM (5 mL) was added TFA (5 mL). The mixture was stirred at 25° C. for 16 h. The reaction solution was concentrated, and the residue was dissolved in water, the pH was adjusted to 7˜7.5 with saturated aqueous of NaHCO3 and extracted with EA. The organic layer was concentrated to give the title product that was used in the next step without further purification (450 mg, crude). LCMS (m/z): 326.2 (M+1).

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with EA
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f6efb4a8a0074cacbef0f5e7ebbe24d8
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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