Hydrochloric Acid → 6-[4-(1-Amino-propyl)-4-trifluoromethyl-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-one

HRID 1948170Notes

Reaction equation

HRID 1948170 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][CH2:19][C:18]([CH:25]([NH2:28])[CH2:26][CH3:27])([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]1.CC(O)C.Cl>O>[NH2:28][CH:25]([C:18]1([C:21]([F:23])([F:24])[F:22])[CH2:17][CH2:16][CH:15]([O:14][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][C:2]=2[Cl:1])[C:9](=[O:12])[NH:8][CH:7]=[CH:6]3)[CH2:20][CH2:19]1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 583808401-[4-(7-Chloro-1-methoxy-isoquinolin-6-yloxy)-1-trifluoromethyl-cyclohexyl]-propylamine

Product 1

HCID 445994996-[4-(1-Amino-propyl)-4-trifluoromethyl-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-oneYield 0.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

160 mg (336 mmol) of 1-[4-(7-Chloro-1-methoxy-isoquinolin-6-yloxy)-1-trifluoromethyl-cyclohexyl]-propylamine (76) were dissolved using 2 ml of 2-propanol and 2 ml of a 1N aqueous solution of HCl. The mixture was treated for 1 h at 100° C. under microwave irradiation. Afterwards, the mixture was diluted using 50 ml of water and lyophilized to yield 154 mg of the desired product. Rt=0.66 min (Method P). Detected mass: 403.2 (M+H+).

Workup

  1. additionThe mixture was treated for 1 h at 100° C. under microwave irradiation
  2. additionAfterwards, the mixture was diluted

Sources & evidence

ORD record
ord-4f594927882441e1a5f60b432f258283
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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