Triethylamine → HCID 57580084, compound

HRID 2425453Notes

Reaction equation

HRID 2425453 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:22])[CH2:10][CH2:11][O:12][CH2:13][C:14]([NH:16][C@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)=[O:15].C(N(CC)CC)C.[Cl:30][C:31]1[C:40]2[C:39]([S:41](Cl)(=[O:43])=[O:42])=[CH:38][CH:37]=[CH:36][C:35]=2[CH:34]=[N:33][CH:32]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:8][N:9]([CH3:22])[CH2:10][CH2:11][O:12][CH2:13][C:14]([NH:16][C@H:17]1[CH2:21][CH2:20][N:19]([S:41]([C:39]2[C:40]3[C:31]([Cl:30])=[CH:32][N:33]=[CH:34][C:35]=3[CH:36]=[CH:37][CH:38]=2)(=[O:43])=[O:42])[CH2:18]1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 221219084-Chloroisoquinoline-5-sulfonyl chlorideHCID 67242570HCID 67242570, compound

Product 1

HCID 57580084HCID 57580084, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-[2-[2-(Dimethylamino)ethoxy]acetyl]aminopyrrolidine trifluoroacetate (246 mg) prepared in Step F in dichloromethane (5 ml) was successively added with triethylamine (387 μl) and 4-chloro-5-isoquinolinesulfonyl chloride (145 mg) at 0° C., and the mixture was stirred at the same temperature for 45 minutes, and further stirred at room temperature for 15 minutes. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and the organic layer was separated. The aqueous layer was extracted three times with chloroform, and the combined organic layer was dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (chloroform:methanol=10:1) to obtain the title compound (160 mg).

Workup

  1. stirringfurther stirred at room temperature for 15 minutes
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted three times with chloroform
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  5. customThe residue was purified by silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-961b0b9a9f57453b91ad6b8b009c8bad
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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