Hydrochloric Acid → 6-[4-(1-amino-3-methoxy-propyl)-4-ethyl-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-one

HRID 1948153Notes

Reaction equation

HRID 1948153 reaction equation
[NH2:1][CH:2]([C:7]1([CH2:14][CH3:15])[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)[CH2:3][CH2:4][O:5][CH3:6].[Cl:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][N:23]=[C:24]2[O:27]C)=[CH:19][C:18]=1F.Cl>>[NH2:1][CH:2]([C:7]1([CH2:14][CH3:15])[CH2:12][CH2:11][CH:10]([O:13][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:17]=2[Cl:16])[C:24](=[O:27])[NH:23][CH:22]=[CH:21]3)[CH2:9][CH2:8]1)[CH2:3][CH2:4][O:5][CH3:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 583808084-(1-Amino-3-methoxy-propyl)-4-ethyl-cyclohexanolHCID 583808287-Chloro-6-fluoro-1-methoxyisoquinoline

Product 1

HCID 583808846-[4-(1-amino-3-methoxy-propyl)-4-ethyl-cyclohexyloxy]-7-chloro-2H-isoquinolin-1-oneYield 43%

Procedure

Example 98 was synthesized using the reaction sequence as described for the alternative synthesis of Example 1 (step d and e). 60 mg of 4-(1-Amino-3-methoxy-propyl)-4-ethyl-cyclohexanol (59) and 53.9 mg of 7-chloro-6-fluoro-1-methoxy-isoquinoline (4) were used to give 43 mg of Example 98 as hydrochloride. Stereochemistry was not assigned. Rt=1.78 min (Method N). Detected mass: 393.3 (M+H+).

Workup

  1. customExample 98 was synthesized
  2. customas described for the alternative synthesis of Example 1 (step d and e)

Sources & evidence

ORD record
ord-62229d892bb64aacaacdb0f6e430224e
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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