tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate → tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylate

HRID 2205611Notes

Reaction equation

C(OC([NH:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[C:24]1[CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH:28]=1)[CH3:13])=O)C1C=CC=CC=1>CCO.[Pd]>[NH2:11][C@H:12]([C:14]1[N:19]=[C:18]2[CH:20]=[CH:21][N:22]([CH3:23])[C:17]2=[CH:16][C:15]=1[CH:24]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25]1)[CH3:13]

Participants

Conditions

Temperature: 27 °C

Procedure

A mixture of tert-butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (900 mg, 1.89 mmol) and Pd/C (100 mg) in EtOH (50 mL) was stirred at 27° C. for 3 hours under H2 (50 psi). The reaction mixture was subsequently filtered, and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC to afford a mixture of the diastereomers of the title compound as a yellow oil (350 mg, 54%). 1H NMR (400 MHz, CDCl3) δ ppm 7.44 (d, J=6.4 Hz, 1H), 7.22 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.2 Hz, 1H), 4.51 (q, J=6.4 Hz, 1H), 3.86-3.37 (m, 1H), 3.76 (s, 3H), 2.31-2.30 (m, 1H), 1.50 (s, 9H), 1.44 (d, J=6.4 Hz, 3H); ESI-MS m/z [M+H]+ calc'd for C19H28N4O2, 345. found 345.

Workup

filtrationThe reaction mixture was subsequently filtered
concentrationthe filtrate was concentrated to dryness
customThe residue was purified by preparative HPLC
customto afford

Sources & evidence

ORD record: ord-6b4fad31638e4dcc89aac73f8b098ee9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371321B2

Reaction notes

Loading…