Water → HCID 86687521, compound

HRID 1473472Notes

Reaction equation

HRID 1473472 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([CH:20]1[CH2:24][CH2:23][CH2:22][NH:21]1)=[N:15][CH:14]=[CH:13]2)(=[O:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:42][O:43][CH2:44][CH2:45]Br.O>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([CH:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH2:45][CH2:44][O:43][CH3:42])=[N:15][CH:14]=[CH:13]2)(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 86687520HCID 86687520, compound

Product 1

HCID 86687521HCID 86687521, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

N-(2,4-dimethoxybenzyl)-1-(pyrrolidin-2-yl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (0.050 g, 0.080 mmol) and potassium carbonate (0.055 g, 0.400 mmol) were dissolved in DMF (0.800 ml). 2-Bromoethyl methyl ether (9.03 μl, 0.096 mmol) was added and the reaction was stirred for three hours at 70° C. Water was added followed by ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layers dried with sodium sulfate, filtered, and concentrated. The material was purified via silica gel column chromatography (12 g, gradient elution 0 to 20% MeOH:EtOAc with 5% triethylamine modifier) to afford N-(2,4-dimethoxybenzyl)-1-(1-(2-methoxyethyl)pyrrolidin-2-yl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as an off white solid. m/z (ESI) 569.3 (M+H)+.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe combined organic layers dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified via silica gel column chromatography (12 g, gradient elution 0 to 20% MeOH:EtOAc with 5% triethylamine modifier)

Sources & evidence

ORD record
ord-c26155da12e246889fc42bb4021d92ed
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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