(S)-tert-Butyl azepan-3-ylcarbamate → HCID 67082393, compound

HRID 875926Notes

Reaction equation

HRID 875926 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2]1.[Br:16][C:17]1[C:18](F)=[C:19]2[C:25]([NH:26][C:27]([CH:29]3[CH2:31][CH2:30]3)=[O:28])=[CH:24][NH:23][C:20]2=[N:21][CH:22]=1>CCCCO>[Br:16][C:17]1[C:18]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:2]2)=[C:19]2[C:25]([NH:26][C:27]([CH:29]3[CH2:30][CH2:31]3)=[O:28])=[CH:24][NH:23][C:20]2=[N:21][CH:22]=1

Participants

4

Reactant 2

HCID 10822534(S)-tert-Butyl azepan-3-ylcarbamateHCID 60205356HCID 60205356, compound

Product 1

HCID 67082393HCID 67082393, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

(S)-tert-Butyl azepan-3-ylcarbamate (431 mg, 2.01 mmol; commercially available or Moon, Sung-Hwan, et al. “An Efficient Conversion of Chiral α-Amino Acids to Enantiomerically Pure 3-Amino Cyclic Amines.” Synthetic Communications. Vol. 28, No. 21 (1998): pp. 3919-3926) was added to N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide (200 mg, 0.671 mmol) in n-BuOH (3 mL), and the reaction was heated for 18 hours to 160° C. in a sealed tube. After concentration, the residue was purified by chromatography (SP4, 25M, water/ACN 100/0→0/100, 40CV) to yield (S)-tert-butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)azepan-3-ylcarbamate (30 mg, 9% yield) as a solid.

Workup

  1. temperaturethe reaction was heated for 18 hours to 160° C. in a sealed tube
  2. concentrationAfter concentration
  3. customthe residue was purified by chromatography (SP4, 25M, water/ACN 100/0→0/100, 40CV)

Sources & evidence

ORD record
ord-4294424a98534c7ea65168770eace6e2
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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