Triethylamine → HCID 59520266, compound

HRID 1162600Notes

Reaction equation

HRID 1162600 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl[S:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:23]([C:26]3[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:33][CH:34]=3)(=[O:25])=[O:24])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 516892Sodium BicarbonateHCID 24730368HCID 24730368, compound

Product 1

HCID 59520266HCID 59520266, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

[4-(4-Isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amine (50 mg, 0.16 mmol), 4-(chlorosulfonyl)benzoic acid (53 mg, 0.24 mmol), triethylamine (45 μL, 0.32 mmol), and DMAP (2 mg, 0.016 mmol) were combined in DCM (2 mL). The resulting reaction mixture was heated in a CEM Exployer PLS™ microwave at 100° C. for 30 min. After cooling to room temperature, saturated NaHCO3 (aq) solution (5 mL) was added. The mixture was extracted with DCM (2×4 mL). The combined organic layer was dried over Na2SO4 and concentrated. Purification of the crude product was carried out using silica gel chromatography eluting with DCM/MeOH 9:1, yielding 4-{[4-(4-isopropyl-phenyl)thiazol-2-yl]-thiophen-2-ylmethyl-sulfamoyl}-benzoic acid. LCMS m/z: 500 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. extractionThe mixture was extracted with DCM (2×4 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of the crude product
  7. washeluting with DCM/MeOH 9:1

Sources & evidence

ORD record
ord-5f05db82e8214d90987bc206fe3352cd
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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