Sodium Hydroxide → 4-(5-Azido-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

HRID 1022860Notes

Reaction equation

[OH-].[Na+].N1CCC[C@H]1C(O)=O.[N-:11]=[N+:12]=[N-:13].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30](I)=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CS(C)=O.[Cu]I.O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[C:30]([N:11]=[N+:12]=[N-:13])=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[N:34][CH:33]=[CH:32]3)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

Under argon atmosphere 40 μL (0.04 mmol) of 1N NaOH, 4.6 mg (0.04 mmol) of L-proline, 3.8 mg of (0.02 mmol) CuI and 15.6 mg (0.24 mmol) of NaN3 were added to a solution of 91 mg (0.2 mmol) of 4-(5-iodo-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester (12) in 2 mL of DMSO. The mixture was heated to 60° C. for 18 h. NaN3, NaOH and L-proline were added in the same amounts again and the reaction was heated to 60° C. for 5 h. After cooling to room temperature water was added. The precipitate was filtered, washed with water and dried in vacuo to give 74 mg of compound 17, which was used without any additional purification.

Workup

temperaturethe reaction was heated to 60° C. for 5 h
additionwas added
filtrationThe precipitate was filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-19da6248913a41e5acdb0365862b6db0
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722671B2

Reaction notes

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