Dimethylformamide → HCID 58958446, compound

HRID 915172Notes

Reaction equation

[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13](=[O:24])OC3C=CC([N+]([O-])=O)=CC=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:28]([CH:31](C)C)[CH2:29][CH3:30])(C)C.[CH3:34][N:35]([CH3:38])[CH:36]=[O:37].[OH-:39].[NH4+]>[Cl-].[Na+].O>[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]([N:28]3[CH2:29][CH2:30][CH2:38][N:35]([C:36]([O:39][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:37])[CH2:34][CH2:31]3)=[O:24])=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Nitrophenyl 5-phenyl-1,3-thiazol-2-ylcarbamate (200.0 mg, 0.59 mmol) along with tert-butyl 1,4-diazepene-1-carboxylate (125.0 ul, 0.64 mmol), diisopropylethylamine (205.5 ul, 2.1 mmol), and dimethylformamide (2.0 ml ) were combined and heated at 60° C. overnight. The reaction was poured into brine (25 ml) containing ammoniumhydroxide (2.0 ml). The mixture was extracted with ethyl acetate (4×25 ml) and the ethylacetate layer back extracted with additional brine/ammonium hydroxide until the yellow color had faded. The ethylacetate layer was dried (MgSO4), and the solvent removed to give tert-butyl 4-{[(5-phenyl-1,3-thiazol-2-yl)amino]carbonyl}-1,4-diazepane-1-carboxylate 24. 1H-NMR (500 MHz, CDCl3): 9.30 (1H, br s), 7.53 (3H, m), 7.37 (2H, t, J=7.81 Hz), 7.28 (1H, t, J=7.08), 3.64 (2H, br s), 3.56 (4H, br s), 3.45 (1H, br s), 3.40 (1H, br s), 1.92 (2H, br s), 1.44 (9H, s). High res. ES MS: Theoretical Mass 403.1798, Measured Mass 403.1801 (C20H26N4O3S+H+)

Workup

extractionThe mixture was extracted with ethyl acetate (4×25 ml)
extractionthe ethylacetate layer back extracted with additional brine/ammonium hydroxide until the yellow color
dry with materialThe ethylacetate layer was dried (MgSO4)
customthe solvent removed

Sources & evidence

ORD record: ord-a8b636a2df874aae86c7aea0c5f7a261
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265134B2

Reaction notes

Loading…