Ethylene Glycol → HCID 58075369, compound

HRID 2370108Notes

Reaction equation

HRID 2370108 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[Cl:5][C:6]1[N:7]=[C:8]([N:21]2[CH2:24][C:23](=O)[CH2:22]2)[C:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[N:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Cl:5][C:6]1[N:7]=[C:8]([N:21]2[CH2:24][C:23]3([O:4][CH2:1][CH2:2][O:3]3)[CH2:22]2)[C:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 86657359HCID 86657359, compound

Product 1

HCID 58075369HCID 58075369, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Azetidin-3-one was reacted with Preparation G in the manner of Preparation Gi to afford 1-(2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)azetidin-3-one. LC-MS (M+H)+=300.0 A mixture of ethylene glycol (119 μL, 2.135 mmol), 1-(2-chloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)azetidin-3-one (320 mg, 1.068 mmol) and 4-methylbenzenesulfonic acid, H2O (20.31 mg, 0.107 mmol) in Benzene (2965 μL) was heated at reflux for 24 h in a Dean-stark apparatus. The resulting mixture was concentrated and purified by Prep-HPLC to afford the title compound. LC-MS (M+H)+=344.0. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.21-7.40 (m, 3 H) 7.15 (d, J=7.63 Hz, 2 H) 4.35-4.53 (m, 4 H) 4.23 (dd, J=9.00, 6.26 Hz, 1 H) 4.03 (s, 4 H) 2.96-3.09 (m, 1 H) 2.80-2.96 (m, 1 H) 2.51-2.70 (m, 1 H) 2.03-2.16 (m, 1 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h in a Dean-stark apparatus
  3. concentrationThe resulting mixture was concentrated
  4. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-402910cec9414871aa40ff4479d630d2
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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