2-tert-Butyl-1,1,3,3-tetramethylguanidine → cis-Tert-butyl 4-fluoro-5-(2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)azepane-1-carboxylate

HRID 876467Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=[C:4]2[CH:3]=1.[F:22][C@H:23]1[C@H:29](OS(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:28][CH2:27][N:26]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:25][CH2:24]1.C(N=C(N(C)C)N(C)C)(C)(C)C>CC#N>[F:22][C@H:23]1[C@@H:29]([O:21][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[C:11]([C:8]2[N:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]4=[N:10][N:9]=2)[CH:20]=[CH:19]3)[CH2:28][CH2:27][N:26]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 40 °C

Procedure

2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol (300 mg, 1.09 mmol) was suspended in CH3CN (5 mL) at ambient temperature, and trans-tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate (454 mg, 1.09 mmol) and 2-tert-butyl-1,1,3,3-tetramethylguanidine (263 μL, 1.30 mmol) were added. The dark solution was stirred at 40° C. overnight, then concentrated to a grey solid which was slurried in water for 10 minutes. The solid was filtered, washed and dried in vacuo to provide the desired product. MS ESI (+) m/z 492.3 (M+1) detected.

Workup

concentrationconcentrated to a grey solid which
waitwas slurried in water for 10 minutes
filtrationThe solid was filtered
washwashed
customdried in vacuo

Sources & evidence

ORD record: ord-66679437cef240f1973853832b2971da
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987251B2

Reaction notes

Loading…