Tert-butyl 1,4-diazepane-1-carboxylate → HCID 86596816, compound

HRID 751422Notes

Reaction equation

HRID 751422 reaction equation
Cl[C:2]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH:17]=[O:18].[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCOCC1>[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:2]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]=2[CH:17]=[O:18])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 46912083HCID 46912083, compound

Product 1

HCID 86596816HCID 86596816, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (210 mg, 0.818 mmol) in 1,4-dioxane (10 mL) is treated with [1,4]diazepane-1-carboxylic acid tert-butyl ester (0.80 mL, 4.11 mmol) and the resulting yellow solution is heated to 110° C. under a reflux condenser for 19.5 hours. The reaction mixture is evaporated to give an orange oil. The residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with dichloromethane, increasing to dichloromethane:methanol (99:1). Fractions containing the product are combined and the solvent evaporated to give 342 mg of 4-(3-formyl-1-phenyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester as a yellow orange glass (99.5% yield). MS: m/e 421 (M+H), 443 (M+Na), 365 (M-C4H8+H), 343(M-C5H8O2+Na), 321(M-C5H8O2+H). 1H NMR (300 MHz, CDCl3): 10.23 (1H, s), 8.49 (1H, d), 8.22 (1H, dd), 7.64-7.48 (3H, m), 7.42 (2H, d), 7.19 (1H, dd), 3.50-3.29 (8H, m), 1.65-1.52 (2H, m), 1.44 (9H, s).

Workup

  1. customThe reaction mixture is evaporated
  2. customto give an orange oil
  3. customThe residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with dichloromethane
  4. temperatureincreasing to dichloromethane:methanol (99:1)
  5. additionFractions containing the product
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-b45406d817cb4bc5b680a8ac1787116d
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

Loading…