4-Toluenesulfonyl chloride → 2'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate

HRID 2059748Notes

Reaction equation

HRID 2059748 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[CH2:8][CH2:7][CH2:6][C:5]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[C:4]=2[N:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:12][C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][C:5]4([CH2:13][CH2:14][CH2:15][CH2:16]4)[C:4]=3[N:3]=[C:2]([NH2:1])[N:11]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178508867HCID 178508867, compound

Product 1

HCID 866343332'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonateYield 15.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 1C (2.91 g, 13.27 mmol), p-toluenesulfonyl chloride (3.79 g, 19.91 mmol), and DMAP (324 mg, 2.65 mmol) in CH2Cl2 (60 mL) was treated with TEA (3.7 ml, 4.40 mmol) at ambient temperature, and the resulting solution was stirred for 3 hours. It was then diluted with CH2Cl2 (100 mL) and H2O (50 mL), and the layers were separated. The organic layer was dried with MgSO4 and concentrated under reduced pressure, then the residue was chromatographed on silica gel (1:2:2 EtOAc/CH2Cl2/hexane, eluant) to provide the title product (750 mg). 1H NMR (300 MHz, CD3OD) δ 7.95 (d, 2 H), 7.44 (d, 2 H), 2.45-2.47 (m, 3 H), 2.40-2.45 (m, 2 H), 1.99-2.10 (m, 2 H), 1.79-1.90 (m, 2 H), 1.65-1.75 (m, 6 H), 1.52-1.62 (m, 2 H). MS (DCI+) m/z 374 (M+H).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was chromatographed on silica gel (1:2:2 EtOAc/CH2Cl2/hexane, eluant)

Sources & evidence

ORD record
ord-74475032326e47cba6ec3899db3e6061
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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