Triethylamine → HCID 86602344, compound

HRID 751523Notes

Reaction equation

HRID 751523 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[C:19](=[O:37])[NH:20][C:21](=[O:36])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH2:32][CH2:33][CH2:34][OH:35])[CH:24]=2)[C:12]2[O:16][CH:15]=[CH:14][C:13]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>O1CCCC1.C(OCC)(=O)C>[CH3:45][S:46]([O:35][CH2:34][CH2:33][CH2:32][N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([C:22]2[C:21](=[O:36])[NH:20][C:19](=[O:37])[C:18]=2[C:11]2[C:12]3[O:16][CH:15]=[CH:14][C:13]=3[CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)=[CH:24]1)(=[O:48])=[O:47]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69270177HCID 69270177, compound

Product 1

HCID 86602344HCID 86602344, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-(5-Benzyloxybenzofur-7-yl)-4-[1-(3-hydroxypropyl)-1H-indol-3-yl]pyrrole-2,5-dione (380 mg, 0.77 mmol) and triethylamine (0.43 ml, 3.1 mmol) in tetrahydrofuran (15 ml) and cool in an ice bath. Add methanesulfonyl chloride (0.066 ml, 0.85 mmol) dropwise, and stir for four hours. Dilute the reaction in ethyl acetate, wash with water and brine, dry with magnesium sulfate, and concentrate to give the title compound (440 mg, 100%). MS(ES+): 571.14.

Workup

  1. temperaturecool in an ice bath
  2. additionDilute
  3. washwash with water and brine
  4. dry with materialdry with magnesium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-258eb9e5f99c42ed85821d5904dc8222
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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