Triethylamine → HCID 25187821, compound

HRID 549444Notes

Reaction equation

HRID 549444 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[N:19]([CH3:20])[C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=1[C:24]([N:26]1[CH2:29][CH:28]([OH:30])[CH2:27]1)=[O:25].C(N(CC)CC)C>C(Cl)Cl>[C:21]([C:18]1[N:19]([CH3:20])[C:15]([NH:14][C:8]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:7]=2[F:6])=[C:16]([C:24]([N:26]2[CH2:29][CH:28]([O:30][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:27]2)=[O:25])[CH:17]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25187543HCID 25187543, compound

Product 1

HCID 25187821HCID 25187821, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methane sulfonyl chloride (0.026 ml, 0.33 mmol) was added dropwise at 0° C. to a stirred solution of Example 27 (102 mg, 0.22 mmol) and triethyl amine (0.047 ml, 0.33 mmol) in CH2Cl2 (1.2 mL). After stirring for 10 min at 0° C., the reaction mixture was allowed to warm up at room temperature. After stirring for 2 hours, the reaction mixture was washed with a saturated solution of NaHCO3, extracted with CH2Cl2. The organics were washed with and brine, dried (MgSO4), and concentrated. Purification by silica gel chromatography gave 100 mg (84%) of the title compound as beige solid. MS (ES) [m+H] calc'd for C18H19FIN3O5S, 536; found 536.

Workup

  1. temperatureto warm up at room temperature
  2. stirringAfter stirring for 2 hours
  3. washthe reaction mixture was washed with a saturated solution of NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe organics were washed with and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-231f34fe43224e1b912cbd7b2940473d
Source dataset
uspto-grants-2011_05
Patent number
US07943659B2

Reaction notes

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