4-Fluorobenzenesulfonyl chloride → tert-Butyl (tert-butoxycarbonyl{6-[(4-fluorobenzenesulfonyl)aminomethyl]pyridin-2-yl}amino)acetate

HRID 2359834Notes

Reaction equation

HRID 2359834 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH2:23])[N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][S:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[N:17]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 86651796Tert-butyl [(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate

Product 1

HCID 86651798tert-Butyl (tert-butoxycarbonyl{6-[(4-fluorobenzenesulfonyl)aminomethyl]pyridin-2-yl}amino)acetateYield 48.1%

Procedure

Reaction and post-treatment were carried out in the same manner as in Reference Example 12-(d) except for using tert-butyl[(6-aminomethylpyridin-2-yl)tert-butoxycarbonylamino]acetate (7.00 g, 20.7 mmol) obtained in Reference Example 12-(c), and using 4-fluorobenzenesulfonyl chloride (4.00 g, 20.6 mmol) in place of 3-pyridylsulfonyl chloride to afford the title compound (4.91 g) as a white solid. (Yield: 48%)

Workup

  1. customReaction

Sources & evidence

ORD record
ord-236f0c9c5b4c4ea88bfbc385708431e2
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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