Water → HCID 44218721, compound

HRID 1928765Notes

Reaction equation

HRID 1928765 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25].O>N1C=CC=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][S:24]([N:23]([CH3:28])[CH3:22])(=[O:26])=[O:25])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 83372Dimethylsulphamoyl chlorideHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44218721HCID 44218721, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)—N2-Indan-1-yl-quinoline-2,6-diamine (0.05 g, 0.18 mmol) was dissolved in pyridine (1 mL). Dimethylsulfamoyl chloride (0.02 mL) was added and stirred for 72 h at ambient temperature. Then water was added and the mixture extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography (silica gel, heptane, ethyl acetate 4:1/1:1) to yield the title compound as a brown oil (30 mg, 43%); MS: m/e=383.6 (M+H+).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-e92ea3c020ee4ca79a2bebb506464a8c
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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