2-Bromobenzoic acid → 4-(2-Bromo-benzoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 1665684Notes

Reaction equation

HRID 1665684 reaction equation
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:41]([O:45][C:46]([N:48]1[CH2:54][CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42]>CN(C=O)C.O>[C:41]([O:45][C:46]([N:48]1[CH2:54][CH2:53][CH2:52][N:51]([C:13](=[O:15])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[Br:10])[CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:42])[CH3:43]

Participants

8

Reactant 5

HCID 69402-Bromobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 578757964-(2-Bromo-benzoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 277.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (460 mg, 0.63 mL, 3.68 mmol) was added dropwise to 2-bromo-benzoic acid (370 mg, 1.84 mmol) in DMF (4 mL). This was followed by the addition of EDCI (423 mg, 2.2 mmol) and HOBT (298 mg, 2.2 mmol). After 2 minutes of stirring, [1,4]diazepane-1-carboxylic acid tert-butyl ester (150 mg, 0.47 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 500 mg (71.12% yield) of 4-(2-bromo-benzoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5aedf342f41482b945e4fa67f833c0f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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