Diisopropylethylamine → HCID 53257344, compound

HRID 576676Notes

Reaction equation

HRID 576676 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH2:20][NH3+:21])[CH:11]=1.C(N(CC)C(C)C)(C)C.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=1[S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>ClCCl>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[C:36]=1[S:42]([NH:21][CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([NH:16][C:12]2[CH:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[O:3][CH3:2])[N:15]=[CH:14][N:13]=2)[CH:18]=1)(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 86672046HCID 86672046, compound

Product 1

HCID 53257344HCID 53257344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

171 mg 3-[6-(2-Methoxy-phenyl)-pyrimidin-4-ylamino]-benzyl-ammonium chloride (prepared in Example 69) (0.5 mmol) was dissolved in 50 cm3 dry dichloromethane, 0.350 cm3 N,N-diisopropyl-ethylamine (259 mg, 2 mmol) was added and the mixture was cooled to 0° C. in an ice bath. After stirring it for 15 minutes 196 mg 2,6-dichlorobenzenesulfonyl-chloride (0.8 mmol) was added and the mixture was stirred for 2 hours at 0° C. and overnight at room temperature. Then 50 cm3 5% NaHCO3 solution was added and it was extracted three times with 50-50 cm3 of chloroform. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated under reduced pressure. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as an yellow solid. Yield: 34 mg (13%). For analitical results and compound identification see Table 1.

Workup

  1. additionwas added
  2. extractionit was extracted three times with 50-50 cm3 of chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residual solid was recrystallized from minimal amount of acetonitrile
  7. customair-dried

Sources & evidence

ORD record
ord-2c1f551a23bd4fba9f9a2d67cdfe9356
Source dataset
uspto-grants-2015_05
Patent number
US09040529B2

Reaction notes

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