4-Allyl-4-amino-cyclohexanol → 6-(4-Allyl-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one

HRID 2370273Notes

Reaction equation

HRID 2370273 reaction equation
FC1C=C2C(=CC=1)C(=O)N(CC1C=CC(OC)=CC=1)C=C2.C(C1(N)CCC(O)CC1)C=C.[CH2:33]([C:36]1([NH2:64])[CH2:41][CH2:40][CH:39]([O:42][C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][C:52]=2Cl)[C:49](=[O:54])[N:48]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)[CH:47]=[CH:46]3)[CH2:38][CH2:37]1)[CH:34]=[CH2:35]>>[CH2:33]([C:36]1([NH2:64])[CH2:41][CH2:40][CH:39]([O:42][C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][CH:52]=2)[C:49](=[O:54])[N:48]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)[CH:47]=[CH:46]3)[CH2:38][CH2:37]1)[CH:34]=[CH2:35]

Participants

4

Reactant 3

HCID 592260294-Allyl-4-amino-cyclohexanolHCID 592260516-(4-Allyl-4-amino-cyclohexyl oxy)-7-chloro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-oneHCID 598182606-Fluoro-2-[(4-methoxyphenyl)methyl]isoquinolin-1-one

Product 1

HCID 592260716-(4-Allyl-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one

Procedure

422 mg of 6-(4-allyl-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (18) were synthesized as diastereomeric mixture starting from 641 mg (2.26 mmol) of 2-(4-methoxy-benzyl)-6-fluoro-2H-isoquinolin-1-one (9) and 370 mg (2.38 mmol) of 4-allyl-4-amino-cyclohexanol (16), following the protocol described for 6-(4-allyl-4-amino-cyclohexyloxy)-7-chloro-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (17). Rt=1.07 min, 1.10 min (Method C). Detected mass: 419.2 (M+H+).

Workup

  1. customRt=1.07 min, 1.10 min (Method C)

Sources & evidence

ORD record
ord-3ac159207fa3437f86df0455b43bcdf4
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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