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

HRID 2386994Notes

Reaction equation

HRID 2386994 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.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.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

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178508867HCID 178508867, compound

Product 1

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

Reagents, catalysts & solvents 3

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

Procedure

A solution of Example 10C (2.91 g, 13.27 mmol), p-toluenesulfonyl chloride (3.79 g, 19.91 mmol), and 4-(dimethylamino)pyridine (324 mg, 2.65 mmol) in methylene chloride (60 mL) was treated with triethylamine (3.7 mL, 4.40 mmol) at ambient temperature, and the resulting solution was stirred for 3 hours. It was then diluted with methylene chloride (100 mL) and water (50 mL), and the layers were separated. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure; then the residue was chromatographed on silica gel (1:2:2 ethyl acetate/methylene chloride/hexane, eluant) to provide the title product. 1H NMR (300 MHz, CD3OD) δ 7.95 (d, 2H), 7.44 (d, 2H), 2.45-2.47 (m, 3H), 2.40-2.45 (m, 2H), 1.99-2.10 (m, 2H), 1.79-1.90 (m, 2H) 1.65-1.75 (m, 6H), 1.52-1.62 (m, 2H); MS (DCI+) m/z 374 (M+H)+.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthen the residue was chromatographed on silica gel (1:2:2 ethyl acetate/methylene chloride/hexane, eluant)

Sources & evidence

ORD record
ord-da68d88d15334b89b886a8925bebcfdf
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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