Triethylamine → HCID 58305643, compound

HRID 2362213Notes

Reaction equation

HRID 2362213 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9](C2C=CC=CC=2N)=[CH:10][CH:11]=1)[CH3:2].C([N:32]([CH2:35][CH3:36])CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C1COCC1.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([N:8]2[C:9]([C:5]3[CH:4]=[CH:36][C:35]([NH:32][S:38]([CH3:37])(=[O:40])=[O:39])=[CH:7][CH:6]=3)=[CH:10][CH:11]=[C:7]2[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])=[C:20]([CH3:28])[CH:21]=1)(=[O:27])[NH2:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 67179328HCID 67179328, compound

Product 1

HCID 58305643HCID 58305643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, 3-[1-(4-carbamoyl-2-methyl-phenyl)-5-(amino-phenyl)-1H-pyrrole-2-yl]-propionic acid ethyl ester (11A, synthesis described in Scheme 4 where R1=4-carbamoyl-2-methylphenyl) (51 mg, 0.13 mmol) was dissolved in 1 mL anhydrous THF. Triethylamine (0.04 mL, 0.26 mmol) and then methane sulfonylchloride (0.01 mL, 0.13 mmol) were added. After 18 hrs, 0.01 mL methane sulfonylchloride was added to push the reaction to completion. After another 18 hrs, the reaction was diluted with water and extracted with EtOAc (3×5 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by preparative TLC plate (5% MeOH/CH2Cl2). 14B, ethyl 3-(1-(4-carbamoyl-2-methylphenyl)-5-(4-(methylsulfonamido)phenyl)-1H-pyrrol-2-yl)propanoate was isolated, rf=0.17 (28 mg, 50%).

Workup

  1. customthe reaction to completion
  2. waitAfter another 18 hrs
  3. extractionextracted with EtOAc (3×5 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by preparative TLC plate (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-44f75fcbb62b481596be238b0daecf7d
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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