Sodium Carbonate → HCID 90121185, compound

HRID 521727Notes

Reaction equation

HRID 521727 reaction equation
ClC(N(C)C)=C(C)C.[C:9]([NH:17][C:18]([NH:20][C:21]1([C:35]2[CH:40]=[N:39][CH:38]=[CH:37][N:36]=2)[CH:25]([CH2:26]O)[CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22]1)=[S:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[C:9]([NH:17][C:18]1[S:19][CH2:26][CH:25]2[CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]2([C:35]2[CH:40]=[N:39][CH:38]=[CH:37][N:36]=2)[N:20]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 90121211HCID 90121211, compound

Product 1

HCID 90121185HCID 90121185, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloro-N,N,2-trimethylpropenylamine (409.71 μL, 3.10 mmol) is added to a stirred solution of tert-butyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-pyrazin-2-yl-pyrrolidine-1-carboxylate (1.09 g, 2.38 mmol) in dichloromethane (30 mL) at room temperature. After stirring the reaction at room temperature for 3 hours a saturated aqueous solution of sodium carbonate (15 mL) is added and the mixture is stirred for 5 minutes. Dichloromethane (80 mL) is added and the layers are separated. The aqueous layer is re-extracted with dichloromethane (70 mL). The combined organic layers are dried over magnesium sulfate and concentrated under reduced pressure. The isolated product is dissolved in methanol (60 mL) and is purified by ion exchange column chromatography eluting with methanol (60 mL) then with 7 M ammonia/methanol solution (120 mL). The basic fraction is collected and the resulting product is further purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title product (747 mg, 71%). ES/MS (m/e) 440 (M+1).

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 5 minutes
  3. customthe layers are separated
  4. extractionThe aqueous layer is re-extracted with dichloromethane (70 mL)
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe isolated product is dissolved in methanol (60 mL)
  8. customis purified by ion exchange column chromatography
  9. washeluting with methanol (60 mL)
  10. customThe basic fraction is collected
  11. customthe resulting product is further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a40325f7eff149e29670326968661594
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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