(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 67045434, compound

HRID 875658Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[Br:14][C:15]1[C:16](F)=[C:17]2[C:23]([NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=3)=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1.CC#N.O>CCCCO>[Br:14][C:15]1[C:16]([N:1]2[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]2)=[C:17]2[C:23]([NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=3)=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1

Participants

Conditions

Temperature: 160 °C

Procedure

(R)-tert-Butyl pyrrolidin-3-ylcarbamate (333 mg, 1.79 mmol) was added to N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (200 mg, 0.597 mmol) in n-BuOH (3 mL), and the reaction was stirred at 160° C. for 24 hours. The reaction was concentrated to dryness, and then the residue was purified by chromatography (SP4, C-18 25M+ column, gradient of 10-90% CH3CN/water, 30CV) to yield (R)-tert-butyl 1-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrrolidin-3-ylcarbamate (105 mg, 35.1% yield) as a solid.

Workup

concentrationThe reaction was concentrated to dryness
customthe residue was purified by chromatography (SP4

Sources & evidence

ORD record: ord-17853b98ba0743f28aaac97920d3ddfa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08981085B2

Reaction notes

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