Sodium Bicarbonate → HCID 178517301, compound

HRID 455265Notes

Reaction equation

[O:1]=[C:2]1[N:6]2[CH2:7][C@H:8]([NH:10][S:11]([C:14]3[C:15](Cl)=[N:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:12])[CH2:9][C@H:5]2[CH2:4][N:3]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1.C([O-])(O)=[O:33].[Na+]>Cl>[O:1]=[C:2]1[N:6]2[CH2:7][C@H:8]([NH:10][S:11]([C:14]3[C:15]([OH:33])=[N:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:12])[CH2:9][C@H:5]2[CH2:4][N:3]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-pyridine-3-sulfonic acid [(6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl]-amide (example 15) (100 mg, 0.21 mmol) was added to concentrated hydrochloric acid (10 mL, 12 M), the mixture was stirred for 24 h at 100° C. To the mixture was added sat. NaHCO3 to adjust to pH=8. Then extracted with ethyl acetate (15 mL×2), dried over anhydrous sodium sulfate and concentrated. The residue was directly purified by pre-TLC (dichloromethane:MeOH=100:1) to yield 20 mg (21%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 12.0 (bs, 1H) 8.22-8.19 (m, 1 Hz), 7.85-7.80 (m, 1H), 7.46-7.41 (m, 2H), 7.11-7.08 (m, 2 Hz), 6.49-6.41 (m, 2H), 4.09-3.91 (m, 4H), 3.63-3.61 (m, 1H), 3.04-3.01 (m, 1H), 2.22-2.20 (m, 1H), 1.64-1.62 (m, 1H); LC-MS: 459.0 [M+1]+.

Workup

extractionThen extracted with ethyl acetate (15 mL×2)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was directly purified by pre-TLC (dichloromethane:MeOH=100:1)

Sources & evidence

ORD record: ord-7d881d1e3d8a4811ab3ca8d6c961eaf4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497288B2

Reaction notes

Loading…