Triethylamine → 4-{4-[3-(6-Propylpyridin-2-yl)ureido]thiazol-2-yl}benzenesulfonamide
Reaction equation
[S:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14](C(O)=O)[N:15]=2)=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].CC[N:21]([CH2:24]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])=CC=1.[CH2:43]([C:46]1[N:51]=[C:50]([NH2:52])[CH:49]=[CH:48][CH:47]=1)[CH2:44][CH3:45]>C1COCC1.O.CCOC(C)=O>[CH2:43]([C:46]1[N:51]=[C:50]([NH:52][C:24](=[O:33])[NH:21][C:14]2[N:15]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([S:1]([NH2:2])(=[O:3])=[O:4])=[CH:10][CH:9]=3)[S:12][CH:13]=2)[CH:49]=[CH:48][CH:47]=1)[CH2:44][CH3:45]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 75 °C
Procedure
In an oven-dried, 50-mL, round-bottomed flask were placed 2-(p-sulfamoylphenyl)thiazole-4-carboxylic acid (250 mg, 0.82 mmol), molecular sieves (800 mg) in THF (20 mL). To this mixture was added Et3N (0.23 mL, 1.64 mmol), followed by DPPA (0.28 mL, 1.28 mmol). The reaction was stirred for 5 min, then 6-propylpyridine-2-amine (280 mg, 2.06 mmol) was added. The suspension was heated to 75° C. for 14 h, cooled to RT, diluted with H2O (10 mL) and EtOAc (150 mL), and filtered to remove molecular sieves. The filtrate was concentrated in vacuo to give the crude product as a yellow solid which was filtered, washed with H2O (3×10 mL), EtOAc (1×10 mL) and Et2O (3×10 mL) to afford the title compound as a yellow solid. MS m/z: 418 (M+H). Calc'd for C18H19N5O3S2: 417.09.
Workup
- temperaturecooled to RT
- filtrationfiltered
- customto remove molecular sieves
- concentrationThe filtrate was concentrated in vacuo
- customto give the crude product as a yellow solid which
- filtrationwas filtered
- washwashed with H2O (3×10 mL), EtOAc (1×10 mL) and Et2O (3×10 mL)
Sources & evidence
- ORD record
- ord-c1f2f9d03f4148bba2c3b9cc5e7d5043
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196104B2
Reaction notes
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