Ammonia → HCID 59332714, compound

HRID 387291Notes

Reaction equation

HRID 387291 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15]1.O[N:29]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.N>CN(C)C=O.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:29])=[O:13])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59332624HCID 59332624, compound

Product 1

HCID 59332714HCID 59332714, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-3-(1,1-dioxido-2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylic acid (0.9 g, 2.007 mmol) was put in a flask and dissolved in N,N-Dimethylformamide (DMF) (2 mL). HOBt (1-hydroxybenzotriazole) (0.271 g, 2.007 mmol) and EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) (1.078 g, 5.62 mmol) were added. The mixture was stirred and 0.5N NH3 in dioxane was added (12.04 mL, 6.02 mmol). The reaction mixture was heated under microwave at 100° C. for 20 minutes. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (50 mL) and extracted with ethyl acetate (3×25 mL). Organic layers were combined and washed with a saturated aqueous solution of sodium bicarbonate, dried (MgSO4) and concentrated in vacuo. The mixture was dissolved in the minimum amount of DCM and precipitated in hexane, giving 0.575 g of the title compound as a pale brown powder.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of sodium bicarbonate (50 mL)
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe mixture was dissolved in the minimum amount of DCM
  7. customprecipitated in hexane

Sources & evidence

ORD record
ord-10fba44721444420a372374292e9eba9
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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