Triethylamine → N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide

HRID 1854288Notes

Reaction equation

HRID 1854288 reaction equation
S([C:5]1[S:9][C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:7][N:6]=1)(=O)(=O)N.NC1C=CC(S(NC2SC(S(N)(=O)=O)=NN=2)(=O)=O)=CC=1.C(N(CC)CC)C.[C:59](Cl)(=[O:69])CCCCCCCCC>C(#N)C>[OH:69][CH2:59][C:5]1[S:9][C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:7][N:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66982Decanoyl chlorideHCID 1345601,3,4-Thiadiazole-2-sulfonamide, 5-(((4-aminophenyl)sulfonyl)amino)-HCID 53318404N-(4-(N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide

Product 1

HCID 53323733N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamideYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(4-(N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)decanamide 139). 5-(4-Aminophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide (7, 50 mg, 0.15 mmol) was suspended in anhydrous acetonitrile (5 mL). Triethylamine (17.1 mg, 0.17 mmol) was added with stirring at 0° C. A solution of decanoyl chloride (32.4 mg, 0.17 mmol) dissolved in anhydrous acetonitrile (1 mL) was added dropwise, and the reaction mixture was stirred at 0° C. for 2 h and overnight at room temperature. Volatiles were removed in vacuo and the residue was washed with water (5 mL). The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 9:1, giving the pure product as a solid (42 mg, 0.09 mmol, 60% yield), mp 242-243° C.; 1H NMR (300 MHz, DMSO-d6) δ 0.84 (t, 3H, J=6.9 Hz), 1.24 (m, 12H), 1.56 (m, 2H), 2.32 (t, 2H, J=7.5 Hz), 7.66 (s, 4H), 7.91 (s, 2H), 10.13 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 14.1, 22.3, 25.2, 28.8, 29.0, 31.5, 36.6, 118.6, 127.0, 137.4, 142.2, 157.8, 170.8, 172.1; LRMS (LCQ, ESI−) calcd for C18H26N5O5S3 488.1, found 488.1 (M−H)−; HRMS (ESI−, m/z) calcd for C18H26N5O5S3 488.1102, found 487.1101 (M−H)−.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred at 0° C. for 2 h and overnight at room temperature
  3. customVolatiles were removed in vacuo
  4. washthe residue was washed with water (5 mL)
  5. washeluted with CH2Cl2:methanol 9:1

Sources & evidence

ORD record
ord-bd74dbe41e2d4c95875b57b4cd6e54de
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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