Triethylamine → HCID 20637897, compound

HRID 1837487Notes

Reaction equation

HRID 1837487 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:13]3[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:12]=3[CH2:11][C@@H:10]3[C:21](=[O:30])[N:22]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:23][C:24](=[O:25])[N:9]23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C1COCC1>[CH2:26]([N:22]1[CH2:23][C:24](=[O:25])[N:9]2[C@H:10]([CH2:11][C:12]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[NH:14][C:13]=3[C@@H:8]2[C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:3][CH:4]=2)[C:21]1=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20637915HCID 20637915, compound

Product 1

HCID 20637897HCID 20637897, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 98 (0.2 g) in THF (5 mL) was added triethylamine (228 μL) and methanesulfonyl chloride (126 μL) and the solution was heated at reflux for 6 hours. After evaporation of THF, the residue was taken up in CH2Cl2, washed with water and dried over Na2SO4. After evaporation of CH2Cl2, the residue was purified by radial chromatography eluting with CH2Cl2/MeOH (95/5) to give the title compound as a brown powder (30 mg) m.p.: 188° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 6 hours
  3. customAfter evaporation of THF
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of CH2Cl2
  7. customthe residue was purified by radial chromatography
  8. washeluting with CH2Cl2/MeOH (95/5)

Sources & evidence

ORD record
ord-792ad5dad5554f5da38e5b35c480352e
Source dataset
uspto-grants-2004_08
Patent number
US06784179B2

Reaction notes

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