Phenyl methyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate → HCID 178484229, compound
Reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=[CH:23][C:15]1=2)C(=O)OC1C=CC=CC=1>C(O)C.O.[OH-].[Na+]>[CH3:1][NH:2][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=[CH:23][C:15]1=2Participants
Conditions
- Temperature
- 78 °C
Procedure
To a stirred solution of phenyl methyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (65 mg, 0.144 mmol) in ethanol (4 mL) was added sodium hydroxide (57.4 mg, 1.436 mmol) as a solution in water (2 mL). The resulting mixture was heated to 78° C. and stirred overnight. The mixture was then cooled to room temperature, diluted with water and sodium hydroxide, and extracted with dichloromethane (5×). The combined organics were dried, filtered, concentrated, and then chromatographed in 10% (2M NH3 in MeOH) in dichloromethane, giving the desired product (22 mg, 46%). 1H NMR (DMSO-d6) δ 7.69 (d, J=3.3 Hz, 1H), 7.56 (d, J=5.1 Hz, 1H), 7.07 (t, J=4.4 Hz, 1H), 6.72 (d, J=8.7 Hz, 1H), 6.53-6.44 (m, 2H), 6.29 (brs, 2H), 3.54-3.51 (m, 2H), 3.3 (m, 2H), 3.04-3.00 (m, 2H), 2.66 (t, J=6.8 Hz, 2H), 2.32 (s, 3H); MS-EI: (m/z, %) 332 (M+, 75), 288 (97), 260 (100); EI-HRMS calculated for C16H20N4S2 (M+), calculated: 332.1129, observed: 332.1145. HPLC: 95% by area.
Workup
- temperatureThe mixture was then cooled to room temperature
- extractionextracted with dichloromethane (5×)
- customThe combined organics were dried
- filtrationfiltered
- concentrationconcentrated
- customchromatographed in 10% (2M NH3 in MeOH) in dichloromethane
Sources & evidence
- ORD record
- ord-733e8538827b43088b7240f22575bfc9
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618286B2
Reaction notes
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