Hydrochloric Acid → 4'-chloro-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

HRID 2059756Notes

Reaction equation

HRID 2059756 reaction equation
CC1C=CC(S(O[C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][C:17]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[C:16]=3[N:15]=[C:14]([NH2:26])[N:13]=2)(=O)=O)=CC=1.[ClH:27]>C(Cl)Cl.O1CCOCC1>[Cl:27][C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][C:17]3([CH2:25][CH2:24][CH2:23][CH2:22]3)[C:16]=2[N:15]=[C:14]([NH2:26])[N:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 866343332'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate

Product 1

HCID 866343344'-chloro-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from Example 1D (300 mg, 0.803 mmol) in CH2Cl2 (10 mL) was added HCl in dioxane (0.6 mL, 4M), and the mixture stirred at ambient temperature for 16 hours. The mixture was concentrated under reduced pressure, and the resulting residue was chromatographed on silica gel, eluting with 5-20% EtOAc/hexane, to provide the title product. 1H NMR (300 MHz, CDCl3) δ 4.79 (s, 2 H), 2.60 (t, J=6.35 Hz, 2 H), 2.02-2.13 (m, 2 H), 1.82-1.92 (m, 2 H), 1.63-1.79 (m, 6 H), 1.55-1.62 (m, 2 H). MS (DCI+) m/z 357 (M+H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was chromatographed on silica gel
  3. washeluting with 5-20% EtOAc/hexane

Sources & evidence

ORD record
ord-f4569003736d4e85ad208ea95dea4f3d
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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