Diisopropylethylamine → HCID 178483096, compound

HRID 1984879Notes

Reaction equation

HRID 1984879 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[C:17]([N:19]([CH3:21])[CH3:20])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Br:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[C:34]([O:42][C:43]([F:46])([F:45])[F:44])[CH:33]=1>C(Cl)Cl>[Br:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][C@H:2]2[CH2:3][CH2:4][C@@H:5]([NH:8][C:9]3[N:18]=[C:17]([N:19]([CH3:21])[CH3:20])[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH2:6][CH2:7]2)(=[O:40])=[O:39])=[C:34]([O:42][C:43]([F:45])([F:44])[F:46])[CH:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 178483084HCID 178483084, compound

Product 1

HCID 178483096HCID 178483096, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of cis-N2-(4-amino-cyclohexyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (680 mg, 2.38 mmol) in CH2Cl2 (7 mL) was added diisopropylethylamine (620 μL, 3.56 mmol). The mixture was cooled on an ice-bath and a solution of 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (849 mg, 2.50 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was stirred on an ice-bath for 6.5 hr. The reaction was quenched with saturated aqueous NaHCO3 The aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 33% EtOAc in hexane) to give cis-4-bromo-N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexyl]-2-trifluoromethoxy-benzenesulfonamide (782 mg, 56%) as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled on an ice-bath
  2. customThe reaction was quenched with saturated aqueous NaHCO3 The aqueous layer
  3. extractionwas extracted with CHCl3 (three times)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (NH-silica gel, 33% EtOAc in hexane)

Sources & evidence

ORD record
ord-b8be823c60044a8483a3fdc6ae3a2291
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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