1-(5-Bromopyridin-2-yl)-1,4-diazepane → 2-(Methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate

HRID 2246225Notes

Reaction equation

HRID 2246225 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:15](=O)([O:22]C1C=CC([N+]([O-])=O)=CC=1)[O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:16][CH2:17][C:18]([NH:20][CH3:21])=[O:19])=[O:22])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 167847331-(5-Bromopyridin-2-yl)-1,4-diazepaneHCID 602095484-Nitrophenyl 2-(methylamino)-2-oxoethyl carbonate

Product 1

HCID 602095672-(Methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylateYield 70.6%

Procedure

The process is performed as described in Example 1 (step 1.2.). Starting with 0.95 g (3.70 mmol) of 1-(5-bromo-2-pyridyl)-1,4-diazepane, obtained in step 11.2., and 0.94 g (3.70 mmol) of 2-(methylamino)-2-oxoethyl 4-nitrophenyl carbonate, prepared in step 2.2. of Example 2, and after chromatography on silica gel, eluting with a 30/70 mixture of ethyl acetate and cyclohexane and then with a 95/5 mixture of dichloromethane and methanol, followed by crystallization from diisopropyl ether, 0.97 g of product is obtained in the form of a white solid.

Workup

  1. customobtained in step 11.2
  2. washof Example 2, and after chromatography on silica gel, eluting with a 30/70 mixture of ethyl acetate and cyclohexane
  3. additionwith a 95/5 mixture of dichloromethane and methanol
  4. customfollowed by crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-46f220c06ccf4577a818991a316a85e7
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

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