Methylamine → HCID 69308466, compound

HRID 1947044Notes

Reaction equation

HRID 1947044 reaction equation
[CH2:1]([S:5][C:6]1[N:11]=[C:10]([N:12]2[C:20]3[C:15](=[C:16]([O:21][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26])[CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:29][CH3:30]>C1COCC1.CCO>[CH3:30][NH:29][S:25]([CH2:24][CH2:23][CH2:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][N:12]2[C:10]1[CH:9]=[CH:8][N:7]=[C:6]([S:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:11]=1)(=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 87778372HCID 87778372, compound

Product 1

HCID 69308466HCID 69308466, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[1-(2-Butylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonyl chloride (10.97 mmol) was dissolved in THF (25 mL) and added dropwise to H2NMe (30 mL) in EtOH at 0° C. and stirred for 30 min, and then allowed to warm to RT The reaction mixture was then poured into ice water, extracted with EtOAc, washed with water and brine, dried with sodium sulfate, filtered, and the solvent removed in vacuo to yield 3-[1-(2-butylsulfanyl-pyrimidin-4-yl)-1H-indol-4-yloxy]-propane-1-sulfonic acid methylamide.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-81a3eab3ca8e46fe9ab304af13c46135
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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