Hydrochloric Acid → 6-{4-[1-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclohexyloxy}-7-chloro-2H-isoquinolin-1-one

HRID 45206Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[O:13]C)=[CH:5][C:4]=1[O:15][CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([NH2:32])([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH3:23])[CH2:18][CH2:17]1.C(#N)C.O>C(O)(C)C>[NH2:32][C:22]([CH:19]1[CH2:18][CH2:17][CH:16]([O:15][C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][C:3]=2[Cl:2])[C:10](=[O:13])[NH:9][CH:8]=[CH:7]3)[CH2:21][CH2:20]1)([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrochloric acid (0.4 mL of a 1M aqueous solution) was added to a solution of 1-[4-(7-chloro-1-methoxyisoquinolin-6-yloxy)-cyclohexyl]-1-(4-methoxyphenyl)-ethylamine (109, 30 mg, 0.07 mmol) in isopropanol (0.4 mL). The reaction mixture was heated in a microwave oven at 100° C. for 30 minutes. Isopropanol was removed under reduced pressure and the remaining aqueous solution freeze dried to give crude product as an amorphous powder. This was treated twice with acetonitrile/water and freeze dried to give 29 mg of the desired product Example 117 as a colourless hydrochloride salt. Rt=2.60 min (Method 2). Detected mass: 410.1 (M—NH3+H+).

Workup

customIsopropanol was removed under reduced pressure
customthe remaining aqueous solution freeze dried
customto give crude product as an amorphous powder
customdried

Sources & evidence

ORD record: ord-3d51e5862d8e4bc18237dac7a978b404
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541449B2

Reaction notes

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