Indole-3-Butyric Acid → HCID 18923906, compound

HRID 1290256Notes

Reaction equation

HRID 1290256 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13](O)=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C.[CH3:36][S:37]([NH:40][C:41]1[CH:42]=[CH:43][C:44]2[O:49][CH2:48][CH:47]([CH2:50][NH2:51])[O:46][C:45]=2[CH:52]=1)(=[O:39])=[O:38]>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][NH:51][CH2:50][CH:47]2[CH2:48][O:49][C:44]3[CH:43]=[CH:42][C:41]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:52][C:45]=3[O:46]2)=[CH:2]1

Participants

6

Reactant 4

HCID 8617Indole-3-Butyric AcidHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 189238797-Methylsulfonylamino-2,3-dihydro-1,4-benzodioxin-2-methanamine

Product 1

HCID 18923906HCID 18923906, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Indolebutyric acid (1.7 g, 8.2 mmole), 1-hydroxybenzotriazole hydrate (1.3 g, 9.8 mmole) and 1,3-diisopropylcarbodiimide (1.5 ml, 9.8 mmole) were combined in 200 ml of DMF and stirred at room temperature for 2 hours under a nitrogen atmosphere. To this was added dropwise 7-methylsulfonylamino-2,3-dihydro-1,4-benzodioxin-2-methanamine (2.0 g, 8.2 mmole) in 50 ml of DMF and the mixture was further stirred for 48 hours. The solvent was removed and the residue partitioned between dichloromethane and water. The separated dichloromethane layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was chromatographed on a silica gel column using ethyl acetate as the eluant. Product fractions were concentrated and washed with a minimum amount of THF to remove a by-product and give 3.0 g (82%) of the desired product, (7-methylsulfonylamino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-4-(1H-indol-3-yl)-butanamide, as an oily white solid.

Workup

  1. stirringthe mixture was further stirred for 48 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe separated dichloromethane layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was chromatographed on a silica gel column
  8. concentrationProduct fractions were concentrated
  9. washwashed with a minimum amount of THF
  10. customto remove a by-product

Sources & evidence

ORD record
ord-2c9c18ab8cf8484b96825251ae3c6f28
Source dataset
uspto-grants-1998_05
Patent number
US05750724

Reaction notes

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