1,2-Dichloroethane → HCID 59591388、化合物

反応式

[CH2:1]([NH:3][S:4]([C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=O)(=[O:6])=[O:5])[CH3:2].[CH3:17][C:18]([C:26]1[S:30][C:29]([NH2:31])=[N:28][N:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>>[CH2:1]([NH:3][S:4]([C:7]1[CH:8]=[CH:9][C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([NH:31][C:29]1[S:30][C:26]([C:18]([CH3:19])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:17])=[N:27][N:28]=1)=[O:14])(=[O:5])=[O:6])[CH3:2]

参加物

反応物 4

HCID 111,2-Dichloroethane

HCID 181649HOAt

HCID 12520985-(Ethylsulfamoyl)-2-fluorobenzoic acid

HCID 234059035-(2-phenylpropan-2-yl)-1,3,4-thiadiazol-2-amine

生成物 1

HCID 59591388HCID 59591388、化合物収率 15.6%

実験手順

To the mixture of 5-[(ethylamino)sulfonyl]-2-fluorobenzoic acid (24.7 mg, 0.1 mmol), prepared according to Scheme 4, and above crude 5-(1-methyl-1-phenylethyl)-1,3,4-thiadiazol-2-amine (21.9 mg, 0.1 mmol) in 2.0 mL of mixed solvents (DCM:DMF=10:1) was added EDC (19.2 mg, 0.1 mmol) and HOAt (13.6 mg, 0.1 mmol). The resultant mixture was stirred at room temperature for overnight, and then concentrated in vacuo. The residue was purified by using a Gilson preparative HPLC system with a Waters Xterra (C-18) column 100 mm by 50 mm ID, eluting with 10% B to 90% B in 10 min, where A=H2O and B=CH3CN pumped at 150 mL/min to yield 5-[(ethylamino)sulfonyl]-2-fluoro-N-[5-(1-methyl-1-phenylethyl)-1,3,4-thiadiazol-2-yl]benzamide (7.0 mg).