Sodium hydride → 5-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclooctylamine

HRID 402546Notes

Reaction equation

HRID 402546 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15](F)=[C:16]([Cl:19])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[NH2:23][CH:24]1[CH2:31][CH2:30][CH2:29][CH:28]([OH:32])[CH2:27][CH2:26][CH2:25]1.C(OC1C2C(=CC(OC3CC(N)C3)=C(Cl)C=2)C=CN=1)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:32][CH:28]3[CH2:29][CH2:30][CH2:31][CH:24]([NH2:23])[CH2:25][CH2:26][CH2:27]3)=[C:16]([Cl:19])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 214902395-Aminocyclooctan-1-olHCID 592248403-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclobutylamineHCID 598182521-Benzyloxy-7-chloro-6-fluoro-isoquinoline

Product 1

HCID 592248335-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclooctylamineYield 30.6%

Procedure

1.3 g of the title compound were synthesized starting from 0.8 g (2.78 mmol) of 1-benzyloxy-7-chloro-6-fluoro-isoquinoline (11), 417 mg (14.4 mmol) of sodium hydride (60%), and 0.63 g (3.5 mmol) of 5-amino-cyclooctanol (60), following the protocol described for 3-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclobutylamine (51). Purification by silica gel chromatography (dichloromethane methanol:aq. ammonia—100:7:0.75) gave 0.35 g of the desired product as a mixture of diastereoisomers. Rt=1.41 min (Method C). Detected mass: 413.1 (M+H+).

Workup

  1. custom1.3 g of the title compound were synthesized
  2. customPurification by silica gel chromatography (dichloromethane methanol:aq. ammonia—100:7:0.75)

Sources & evidence

ORD record
ord-7c8c328b53d247bab73fbf4c49578c3f
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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