(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 58317729, compound

HRID 2092856Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])[CH2:10][C:6]=2[C:5]([F:23])=[C:4](Cl)[N:3]=1.[NH:25]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26]1>C(#N)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=3[O:20][CH3:21])[CH2:10][C:6]=2[C:5]([F:23])=[C:4]([N:25]2[CH2:29][CH2:28][C@H:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:26]2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A tube containing 4,6-dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (300 mg, 0.808 mmol) and (S)-tert-butyl pyrrolidin-3-ylcarbamate (301 mg, 1.616 mmol) dissolved in ACN (4 mL) was sealed and heated at 100° C. for 2 d. The reaction mixture was concentrated and dissolved in EtOAc (20 mL) and washed with saturated aq NaHCO3 (10 mL) and brine (10 mL). The organic extracts were dried over Na2SO4 and evaporated to give a crude product, which was purified via preparative HPLC. Pure fractions were collected and evaporated to give the title compound (235 mg, 55.8%). [M+H] calc'd for C25H30ClFN4O5, 521. found, 521.

Workup

customwas sealed
concentrationThe reaction mixture was concentrated
dissolutiondissolved in EtOAc (20 mL)
washwashed with saturated aq NaHCO3 (10 mL) and brine (10 mL)
dry with materialThe organic extracts were dried over Na2SO4
customevaporated
customto give a crude product, which
customwas purified via preparative HPLC
customPure fractions were collected
customevaporated

Sources & evidence

ORD record: ord-e2e4e83c1fa241808c05288cccb35814
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440689B2

Reaction notes

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