Hydrochloric Acid → 6-[(1S,4S,5S)-5-(1-Amino-propyl)-5-phenyl-bicyclo[2.2.1]hept-2-yloxy]-7-chloro-2H-isoquinolin-1-one

HRID 45193Notes

Reaction equation

HRID 45193 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12]C)=[CH:4][C:3]=1[O:14][CH:15]1[CH2:20][C@@H:19]2[CH2:21][C@H:16]1[CH2:17][C@@:18]2([CH:28]([NH2:31])[CH2:29][CH3:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(O)C.Cl>O>[NH2:31][CH:28]([C@@:18]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:17][C@@H:16]2[CH2:21][C@H:19]1[CH2:20][CH:15]2[O:14][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[C:9](=[O:12])[NH:8][CH:7]=[CH:6]2)[CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 583809411-[(1S,2S,4S)-5-(7-Chloro-1-methoxy-isoquinolin-6-yloxy)-2-phenyl-bicyclo[2.2.1]hept-2-yl]-propylamine

Product 1

HCID 583809246-[(1S,4S,5S)-5-(1-Amino-propyl)-5-phenyl-bicyclo[2.2.1]hept-2-yloxy]-7-chloro-2H-isoquinolin-1-oneYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

35 mg of 1-[(1S,2S,4S)-5-(7-Chloro-1-methoxy-isoquinolin-6-yloxy)-2-phenyl-bicyclo[2.2.1]hept-2-yl]-propylamine (90) were dissolved using 1 mL of 2-propanol and 1 mL of a 1N aqueous HCl-solution. The mixture was heated to 100° C. for 1 h under microwave irradiation. Afterwards, 20 mL of water were added and the mixture freeze dried. The residue was once again treated with 20 mL of water and freeze dried to yield 34 mg of the desired product as its hydrochloride. Rt=0.75 min (Method 18). Detected mass: 423.2 (M+H+)

Workup

  1. customthe mixture freeze dried
  2. additionThe residue was once again treated with 20 mL of water and freeze
  3. customdried

Sources & evidence

ORD record
ord-50ae8c6b158d4c98aefef285925d7082
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

Loading…