5-Fluoroindole-2-carboxylic acid → HCID 22065999, compound

HRID 1828275Notes

Reaction equation

HRID 1828275 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25](O)=[O:26])=[CH:19]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1)=[O:26])=[CH:19]2

Participants

5

Reactant 3

HCID 18205-Fluoroindole-2-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 22065999HCID 22065999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1,4-diazepane-1-carboxylate (2.0 g, 10 mmol, Aldrich), 5-fluoro-1H-indole-2-carboxylic acid (1.79 g, 10 mmol, Aldrich), and EDCI (1.92 g, 10 mmol) were combined in CH2Cl2 (30 mL) at room temperature and stirred for 24 hours. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CD3OD, 300 MHz) δ 1.46 (s, 9H), 1.86–2.14 (m, 2H), 3.40–3.58 (m, 2H), 3.62–3.72 (m, 2H), 3.75–4.05 (m, 4H), 6.78 (s, 1H), 6.99–7.09 (m, 1H), 7.28–7.35 (m, 2H); MS (DCI/NH3) m/z 362 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7687c6dbef5d48519c87564e7a195391
Source dataset
uspto-grants-2006_06
Patent number
US07057042B2

Reaction notes

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