Pyridine → N-3',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-ylbenzamide

HRID 853890Notes

Reaction equation

HRID 853890 reaction equation
[N:1]1[CH2:2][CH2:3][CH2:4][N:5]2[C:13]3[CH:12]=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=3[C:7]3([O:19][CH2:18][CH2:17][CH2:16][O:15]3)[C:6]=12.N1C=CC=CC=1.C(Cl)Cl.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[N:1]1[CH2:2][CH2:3][CH2:4][N:5]2[C:13]3[CH:12]=[CH:11][C:10]([NH:14][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:9][C:8]=3[C:7]3([O:19][CH2:18][CH2:17][CH2:16][O:15]3)[C:6]=12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 116804673',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-amine

Product 1

HCID 11710287N-3',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-ylbenzamideYield 15.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold solution of 3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′-amine (0.290 g, 1.44 mmol) and pyridine (0.349 mL, 4.32 mmol, 3 eq) in anhyd. CH2Cl2 (14.4 mL) was added benzoyl chloride (0.200 mL, 1.73 mmol, 1.2 eq) drop-wise with cooling in an ice bath under a dry N2 atmosphere. After stirring 2 hr. at room temperature the reaction was added to water. The reaction mixture was washed with Et2O (3×), basified with 2.5N NaOH and extracted with EtOAc (4×). The combined organic extracts were concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3O H/NH4OH (98/1/1) to give the title compound as a yellow solid (0.079 g, 15% yield). NM (300 Mz, DMSO-d6): consistent.

Workup

  1. temperaturewith cooling in an ice bath under a dry N2 atmosphere
  2. washThe reaction mixture was washed with Et2O (3×)
  3. extractionextracted with EtOAc (4×)
  4. concentrationThe combined organic extracts were concentrated
  5. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3O H/NH4OH (98/1/1)

Sources & evidence

ORD record
ord-8caf6469c14d4bef8c739b3f6cc09df9
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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